The Road Goes Ever On
by Amrywiol
Summary: This is the 2nd part of "The Road Not Taken" series and continues from the end of the first and probably won't make much sense if you haven't read that - but just in case, Jeff's still a lawyer and never went to Greendale and five years into the timeline he's just met Annie for the first time (spoiler summary for the first part is given as an opening note to the main story).
1. Chapter 1

_**Author's Note:**_ _Previously on "The Road Not Taken"... Alan Connor died of overwork (official version)/massive cocaine overdose (universally believed version) before he could expose Jeff's fake degree, allowing Jeff the opportunity to properly cover his tracks and go on from success to success in the legal field, ending TRNT as a partner with Mark in their own firm. The rest of the study group navigate their Greendale years without him to some degree - Pierce leaves/is expelled earlier than in the Prime Timeline and Annie goes to Delaware with Vaughn, but returns after a year with a revised master plan. By the start of this story it's just over four years later and Greendale is being sued for incompetent education standards after a bridge collapsed upstate. The college has engaged Jeff's firm to defend it, and a sharply dressed lawyer with extremely good hair has just met a hyperactive type-A student (also with extremely good hair) for the very first time..._

XXXXXX

Jeff Winger was appalled.

He'd arrived at Greendale that morning expecting a pretty straightforward case and nothing he'd heard from the dean had led him to believe otherwise, for all that he'd enjoyed horrifying the man with visions of an apocalyptic outcome.

But then he'd listened to the girl - _Annie, her name was -_ talk him through the records she was organising (he pretended not to hear the bit where she talked about the dean "joking" about shredding them) with increasing disbelief.

(" _This_ is a degree thesis?" Jeff said at one point, holding up a flimsy model of a bridge made out of lego bricks.

Annie's bouncy optimism faded somewhat. "You have to understand Greendale isn't a rich school," she said, not quite meeting his eyes. "Sometimes we just have to make do.")

It all led Jeff to one conclusion. _There's no way I can allow this to go before a jury. If the other side turn this into a trial of this school's academic standards we're screwed - I have to kill it before it gets that far._

"Sorry?" he said instead, Annie had said something while he was ruminating.

"I asked what you thought our chances were."

He winked at her. "You're safe with me Annie, that's the Winger guarantee." The smile that lit up her face was worth the small lie. "What do you say we get out of here and -"

" _What the hell are you doing here?"_ A surprised voice called out.

Jeff and Annie both turned towards the door at the same time to see who had spoken.

"Britta?"

" _Britta?"_

They turned to face each other, a moment of realisation dawning on each of them.

"You're _that_ Annie?"

" _You're_ Booty Call Guy?" Annie looked at him with new eyes, blushing slightly as she remembered some of the - frankly lurid - stories Britta had told (usually while extremely drunk) about their hook-ups. _She never went into detail about how good looking he was though -_

" _Booty Call Guy?_ Objectification much, Britta?" Jeff said, fortunately for Annie he'd turned to face Britta and missed her moment of confusion.

"Ooh, plot twist," this from a Middle-Eastern looking young man standing next to an African-American man and woman.

"And these must be the rest of your friends." Jeff said, looking at Britta who glared back at him.

When the noise finally died down and everybody had sat down, Jeff asked (with somewhat frosty politeness) just what they were doing there.

"We're the Staff-Student Liaison Committee," Britta said, a grin on her face that suggested she knew exactly why Jeff was irritated at being interrupted. "Annie, Abed and I are the students, Shirley runs the snack bar and represents the franchise holders and Troy keeps the air conditioning from dying on us and represents the maintenance staff."

"Shirley and I graduated last summer!" Troy said with a grin on his face as though he could barely believe it - Jeff had heard enough stories from Britta of her cute-but-dim, on/off boyfriend that he barely believed it either.

"Wasn't there anybody from the teaching staff available?" Jeff thought he kept the sarcasm in his voice restrained in the circumstances.

"That would be me," a cheery, British accented voice announced the latest arrival.

"Duncan?" Jeff cried out in disbelief. "As if this day couldn't get any better…"

"You know him, too?" Annie said.

XXXXXX

That evening Jeff Winger had a lot to think about. He was supposed to be thinking about the case - he'd brought a couple of boxes full of the most important papers home with him to read after all, but other than fire off a few text messages to his Associates asking them to do some research for him he'd barely looked at them.

Instead, as he stood on the balcony of his apartment looking out over the fashionable Central Business District with a glass of Scotch in his hand he cast his mind back to the strange assortment of people he'd met that day. Britta of course he was familiar with, as he was with Duncan, for all that he hadn't seen him for some years (and the way Duncan looked at Britta at times explained why the drunken slacker had volunteered for the committee).

The housewife (who was another one who invoked a nagging sense of familiarity in Jeff for reasons he couldn't identify) couldn't seem to decide whether he was the hottest thing she'd seen since Denzel Washington last went shirtless or a shameless sinner who should be kept well away from her friends. Jeff was confident enough he'd be able to handle her without too much difficulty.

The guys - Troy and Abed - had barely been a problem at all, and seemed to have been fully won over when Jeff 'allowed' them to carry the boxes of papers to his car. The awe they'd shown at being allowed to touch a real, live Ferrari had been very gratifying - unlike Annie, who'd walked with them and didn't seem to know enough about cars to know she was supposed to be impressed.

Ah yes, Annie. Annie, Annie, Annie. Annie with her severe blouse, pastel cardigan, knee-length skirt and sensible heels. Annie who, despite only being a student had, through sheer force of personality and work ethic managed to seize control of the school archives and cow the dean into doing her bidding to the extent that the "staff-student liaison committee" consisted entirely of her friends/underlings (and Ian Duncan). Annie, who Jeff had pegged within minutes as being the one person he absolutely had to have on his side if he was to have maximum freedom to run the case the way he wanted to. Normally Jeff's opinion of hard work, discipline and organisation was similar to his opinion of virginity, sobriety and off-the-rack fashion - much overrated qualities best found in others. Annie however brought an undeniable charm to her particular brand of control freakery.

The were other reasons to like the small-but-perfectly-formed brunette with huge blue eyes and a sunny smile of course and it flummoxed Jeff slightly to think that she hadn't so much as turned down his initial overtures to move things onto a more… informal basis as not even noticed them. _The race is not to the swift, nor the battle to the strong,_ he thought and smiled suddenly at the memory of his mother's needlework, one of the few things from his childhood he didn't loathe. He had no idea where Doreen Fitzgerald had got the line from.

XXXXXX

(Apartment 303, same evening)

"Annie, you have to seduce Jeff."

" _Abed!_ " Annie was shocked. Oh, she couldn't deny (to herself at least) that the ridiculously good looking and expensively dressed lawyer had intruded on her thoughts in ways that weren't… entirely linked to the case, but still! "Why on earth would you say that?"

"His car would be perfect for the film I'm making for my degree project," Abed said as though it was obvious. "And he won't lend it to me without an incentive."

" _Abed!"_ Annie was starting to hyperventilate.

"I don't see what the problem is," Abed said blandly. "Your genetic markers are optimised to appeal to a man like Jeff-"

"Dude?" Troy looked thoroughly confused.

"Annie's hot." Abed explained.

"Ahhh," Troy nodded understandingly.

"-and his genetic markers are optimised to appeal to a woman like you." Abed continued talking to Annie as though the distraction hadn't happened. "And according to Britta his sexual technique is perfectly satisfactory if somewhat emotionally disengaged so it's not as if-"

"AAAAAAAAARRRRRRGGGGGHHHHH!" Annie pivoted on a heel and stormed off, slamming her bedroom door behind her.

"What did I say?" Abed looked baffled.

"Oh, buddy…" Troy said.

XXXXXX

"So, how's the case looking?" Mark said. It was the next day and as they tried to do at least once a week the senior partners of Petrocelli & Winger were meeting for lunch to informally discuss their week and ensure there were no surprises lurking.

"It should be straightforward…" Jeff sighed.

"But?" Mark replied.

"It seems to be a good place, and the people who go there are incredibly loyal -" Jeff found himself thinking of Annie and her friends again "- but the academic standards are terrible!"

"A bit of a drawback in a school," Mark said dryly.

Jeff nodded. "If this goes to trial we run the risk of a jury looking at the bridge made out of construction bricks that Humphries submitted for his degree thesis and ignoring the law to say _of course_ he couldn't have learned what he needed to know."

Mark paused for a moment, sighing happily as he chewed oh a generous helping of Linguine Carbonara before speaking further. "So what are you going to do?"

"Kill it before it gets that far of course," Jeff said grimly. "Chloe and Michaela-" naming the Associates he'd texted the night before "-have come up with a couple of promising avenues I'll be looking into further. I'm heading back to the school this afternoon to meet up with my main contact there and develop some options." _Japanese or French, maybe a bar afterwards…._

"The dean?"

"Good grief, no - he's part of the problem. He's so pathetically eager to be liked that he's never taken a hard decision in his life. No, it's the student chair of the staff-student committee, who's basically taken control of the committee and the school's response. The dean's too disorganised to recognise a power play when he sees one and is only too happy to let her get on with it."

"Her? Oh Tango…" Mark shook his head in mock disapproval. "Is she cute?"

"I can't say I noticed," Jeff replied primly.

XXXXXX

"Hi Jeff!" Annie greeted him with a sunny smile. It was four o'clock in the afternoon and the campus was almost empty.

"Sorry I'm late Annie-" their appointment had been for half an hour previously "-I got delayed by the dean." Jeff had popped into the dean's office as a courtesy when he had arrived only to be detained for half an hour of increasingly dubious innuendo.

Annie rolled her eyes in sympathy. "Try to be flattered, it means he probably likes you…"

"I'll try," Jeff replied dryly. "Fun though this is-" he winked at Annie, who blushed slightly "-I'm here on business. Do you have anything for me?"

Annie nodded, dipped below the table and came up again holding a dozen files in her hands. "As you asked for, I've compiled a dossier on each of Humphries' teachers -" she slid the pile over to Jeff -"including a summary of their courses."

Jeff pulled one out of the pile at random. "Professor Donald Crewitt?"

Annie's smile turned forced. "He worked on the Hoover Dam as an apprentice - we're really lucky to have him!"

"That's g- wait, _Hoover Dam?_ That would make him-" Jeff opened the file, checked Crewitt's personal details and did a quick mental calculation "-ninety-seven years old!"

Annie desperately tried to stay positive, but couldn't quite look Jeff in the eye. "He has a couple of pensions so doesn't ask for much in the way of salary and teaching keeps his brain active. He really is surprisingly spry for - are you alright?" Jeff's head was in his hands while he massaged a spot between his eyes.

 _The more I hear about this place…_ he thought to himself. "Stress headache," he said.

Annie waved dismissively. "Oh I've had those since I was four. I've gotten used to it."

"I wish I could say I was surprised," Jeff's smile turned sympathetic before he put Crewitt's file back on the pile and shifted back to business mode. "I'll read these over the weekend, in the meantime-" he pulled out his tablet and started working through a list of observations.

(An hour and a half later)

"I think that's enough for today," Jeff said as he hit the off switch on his tablet, vaguely wishing for the days when he could dramatically slam a notebook shut - _No! I'm too young to reminisce about the good old days! Especially -_ he shut down that line of thought as Annie nodded and stretched distractingly. "Do you want to head out for something to eat? My treat."

Annie briefly looked tempted, then her expression went sombre. "CBA rule 1.8.j. Jeff," she said as she shook her head.

Jeff looked baffled for a moment, then a broad grin spread across his face. "Have you been looking up the rules for when it's appropriate for a lawyer and client to sleep together, Annie?"

"It's not like that!" Annie went bright red with embarrassment. "The dean asked me to look it up! 'For a friend' he said!"

Jeff's smirk faded. He really wanted to believe Annie was deflecting, but on the other hand he'd met the dean...

"And anyway," Annie continued. "I promised to spare some time for Abed and Troy tonight - Abed owes me an apology for something and with those two that usually involves a multimedia presentation and costumes." She rolled her eyes again and finished packing. "See you on Monday, Jeff?" she said, slightly wistfully.

"Yes you will," Jeff smiled in a way that made her blush slightly as she smiled back. "Before you go -" he reached into his pocket, took out a small metal case and extracted a card. "Take this, in case you think of anything."

Annie looked down at the business card and turned it over - it felt like silk in her hands. _I wonder how much this cost?_ "I will Jeff," she said. "Thanks - see you Monday," she repeated before grabbing her case and skipping past Jeff. He watched her go, his mouth slightly open with surprise. _Well, that was… something._

XXXXXX

Annie almost ran out of the library and across the campus to her parked car, determined to get away before she gave in to temptation. Oh, the part of Annie that remembered she'd had a bad year-long relationship and thought she deserved a break was seriously tempted by the cocky, well-dressed lawyer's offer. But the part of Annie that was sensible and always tried to be in control - _don't let him get under your skin Annie,_ she thought to herself as she kept her head down and concentrated on not turning around. _His world is one of expensive cars, expensive clothes and expensive women. There's no way you could fit into that world with your thrift store clothes and community college education - he'll use you until he gets bored or embarrassed and then abandon you. No, keep this friendly and constructive and strictly business focussed and you'll be safe. You need to be the one in control, not him._ Thus resolved, she took out her phone and the business card Jeff had given her.

XXXXXX

Jeff was feeling slightly out of sorts - he was sure Annie had been about to accept his invitation before she changed her mind and basically fled the scene. He was starting to wonder what exactly he was doing wrong, so he replayed the conversation in his head as he packed his briefcase and started walking back to the Ferrari. He was just over halfway there when his phone vibrated with an incoming text message, he saw it was an unknown number, shrugged, swiped and opened it.

 _Just testing - now you've got my number too! Annie_

Jeff clicked on the icon to create a new contact. He didn't notice the soft smile on his face as he did so.

XXXXXX

Greendale Community College, September 2nd 2013

" _Three hundred dollars an hour!"_ Annie yelled. "How can you possibly justify gouging a not-for-profit public college for that sort of money?"

 _Did she just jump out of a bush?_ \- lt was Jeff's third day on the case and he hadn't seen her approach as she ambushed him as he walked into Greendale. _The dean must have showed her our rates,_ he thought. _The devious little weasel is probably hoping those baby blues will get him a discount. Although -_

"Annie, has anybody ever told you you're spectacularly hot when you're angry?"

"What, oh…" Annie's rage had suddenly been replaced by a blush and an embarrassed smile.

"And _that's_ how I justify my fees," he said with a smirk. "By being the best in the state at what I do. In this case, by distracting you for long enough that you don't even notice me walking away with the win."

Despite having just had it explained to her, Annie allowed herself to be distracted. "And what is the win here, Jeff?"

Jeff's smirk got even wider. "You, in a hot dress, having dinner with me tonight."

Annie snorted, though she couldn't quite keep the blush and the smile off her face. "Not going to happen, counsellor. We have a case to prepare for."

Jeff didn't look the slightest bit put out by being shot down. Instead he shifted back to professional mode. "And that's the other way I justify my fees. There isn't going to be a case."

" _What?"_

"Do you have a suit, Annie?"

Annie looked thoroughly knocked off balance at Jeff's continual changes in direction. He smiled as though he knew what effect he was having.

"What do you mean?" She said.

"You know - knee length black skirt, fitted jacket, white blouse, medium heels…"

"I know what a women's suit is Jeff - and yes, I have one." Annie's voice was acquiring a sharp, get-to-the-point edge.

"I've arranged a meeting with Humphries' attorney at two this afternoon - change into your suit and you can sit in on it." Annie's eyes opened wide with surprise. "I'm willing to make a bet with you that by ten minutes after we sit down this case will be dead."

Annie's competitive instincts woke up. "You're on. What's the stake?"

Jeff smirked cockily as he sprung his trap. Too late, Annie realised what was coming. "You, in a hot dress, having dinner with me tonight." He repeated.

Annie rolled her eyes, but she didn't bother to suppress a smile. "And if you lose?"

Jeff's grin didn't budge. "Then you buy me dinner."

"Har, har counsellor." Annie met his gaze head on. "Troy and Abed get to borrow that Ferrari of yours for a day."

Jeff was speechless for a moment. _This girl is even sharper than I've been giving her credit for,_ he thought. He visibly swallowed his sudden nerves. "Deal," he said.

Annie tilted her head sideways and smiled - despite her promise to herself not to be taken in by his charm and self-confidence, she was impressed he hadn't backed down after her counter-offer. She turned on a heel and skipped out the door. "Now if you'll excuse me, I've got to dig out my interview suit and get changed. See you at two, Jeff."

XXXXXX

Jeff Winger's office, 1:54PM

"Shouldn't the dean be here?" Annie said. "Oh thanks," she added with a smile - Jeff had spotted her nerves and handed her a Scotch from his minibar.

He gave her a small grin. "I convinced him that client representation at his level would send the wrong message - they would think we were scared. Instead, a more junior level of representation - a student councillor, for example-" Jeff raised his own glass in mock salute "-would send the appropriate message of disdain."

Jeff's secretary popped her head round the door. "Mr Humphries and his attorney are waiting in Meeting Room G, Mr Winger."

"Thank you Maria," he said.

"We're up," he added, turning to Annie. He moved to hold open the door, as she walked past him his hand dropped into place in the small of her back to ease her through ahead of him. She fought to suppress the slight tingling sensation.

(Meeting Room G)

Jeff ushered Annie in ahead of him, they took their seats and Jeff put his folder on the table in front of him with his phone next to it, discreetly activating the timer on it. Introductions were made - Humphries' attorney was a small, balding man who was sweating even in the air conditioned room - for the first time in years, Jeff thought of Alan Connor. He shook his head slightly to rid himself of the memory.

"Shall we get down to business?" the sweating man said. "My client is willing to be reasonable and would be prepared to entertain a settlement offer along the lines of a cash sum-" he passed a piece of paper across the table, Jeff didn't pick it up "- and an admission of liability on the part of Greendale for providing a substandard education."

"We have a counter offer," Jeff opened his folder and slid something over.

"What is this?"

"Colorado Revised Statute Title 12, Article 25 Part 1. I draw your attention in particular to clause 114-" Jeff paused while the sweating man leafed through the document.

"As you will see, obtaining a licence to practice as a professional engineer in this state is a lengthy process consisting of several stages, of which attaining a recognised degree such as the one Greendale offers is only the first. Mr Humphries has been representing himself as an engineer based solely on his degree, hence this suit."

Sweating man had gone deathly pale. Jeff bared his teeth in a way that could not be mistaken for a smile. "You have one chance to apologise and leave, and if you don't I will pass everything I have to the State Board of Licensure to commence criminal action for practising engineering without a license."

"But I only-" Humphries spoke for the first time.

" _Shut up._ " Sweating man hissed. "I apologise for the misunderstanding Mr Winger, Ms Edison - we'll take up no more of your time and I will write to the court formally withdrawing the action as soon as I return to-"

"That won't be necessary," Jeff passed another piece of paper over. "Sign here-" he pointed at the bottom of the page. Sweating man looked like he wanted to murder Jeff, but he signed and grabbed his client's elbow and hurried him out of the room. Jeff waved them goodbye, reached for his phone and stopped the timer then turned and showed it to Annie.

"Six minutes, forty two seconds," he said. "I hope you like French food, I've booked the restaurant for seven." His smile was huge, Annie for once was speechless as he handed over a card with the restaurant's address on it.


	2. Chapter 2

Chapter 2

 _Previously on "The Road Goes Ever On"._

 _MR WINGER, a dashingly handsome cad with a dubious moral compass has found himself captivated by the passion, energy and optimistic worldview of MISS EDISON. Through the use of a dubious strategem that took advantage of her competitive nature he has inveigled her to accompany him to dinner at an establishment of his choosing. Tune in to this week's episode to see how events unfold..._

XXXXXX

"Annie, you don't have to do this - you're a strong, independent woman not some carny prize!" Britta had stormed over to Apartment 303 as soon as she'd heard about the bet (Troy, bless him, had tweeted it), and was in the process of haranguing Annie while she attempted to prepare. The boys, sensibly, had retreated to the TV area while they argued.

Annie stopped brushing her hair at that point to concentrate on giving her friend her best 'really, Britta?' glare - the blonde at least had the decency to break eye contact and blush slightly as she remembered a night handcuffed to Annie's radiator (she'd never quite dared to ask why Annie had handcuffs in her bedroom) screaming to be let loose so she could run to Blade. "I thought we agreed long ago that I'm not a role model," Britta sighed. "Don't do stupid stuff just because I do, okay? And going out with a guy like Jeff Winger because you lost a bet is really stupid!"

"It's _one date_ Britta - I made a promise and I have to keep it!" Annie had on her defiant face as she tossed her hair slightly. "And anyway, I thought he was your friend - the one you never told us about -"

"I told you about him," Britta mumbled.

"'Booty call guy' is not a name, Britta!" Annie was - just - holding on to her patience. "How bad can it be, anyway?"

"Oh, it won't be bad." Britta sighed as Annie humphed in exasperated confusion. "He'll take you somewhere really nice, spend an evening flattering you shamelessly and generally making you feel like the most important and desirable woman in the world and, at the end of it, he'll invite you back to his place and you'll feel really tempted to go."

"I'm really not seeing the problem, Britta." Annie had given up trying to brush her hair and instead had crossed her arms over her chest while she looked at the other woman, her head tilted slightly.

"Jeff Winger likes women," Britta finally said. "He _really_ likes women-"

"Britta…" Annie's patience was fraying.

Britta paused for breath and carried on speaking. "But he doesn't believe in true love or happily ever afters - he thinks it's all a scam invented to keep greeting card manufacturers, florists and divorce lawyers in business - 'nut up and die alone' is his philosophy. You'll never be his Miss Right - no woman will be - the most you'll be is Miss Right Now. You've always wanted more than that Annie, you deserve more than that."

Annie looked temporarily shaken by her friend's bleak analysis. "It's only one date Britta," she repeated as she visibly gathered herself. "Look - you know what my dating history's been like over the last year. I spent almost two months seeing another guy who was in denial about himself - and seriously, what is it about me that attracts guys like that? Not a word, Abed-" she'd spotted him sit up as though about to say something "-and the rest of the time I was in a relationship with somebody who didn't even exist!" Abed slipped back into his seat.

"I just think I deserve one evening with a cute guy who's going to spend the evening making me feel like - what was it again?" Annie's eyes seemed to double in size and start to glisten slightly.

 _Oh no, not the puppy face!_ Britta said to herself. "The most important and desirable woman in the world," she sighed instead.

Annie's face lit up in a brilliant smile as though a switch had been flicked. "That's it! Now if you'll excuse me, I really do have to finish getting ready if I'm going to get my bus-"

"You don't have to worry about that-" Britta looked over to Abed and Troy, who nodded "-we've discussed it and we're going to give you a lift in then catch a film for the evening and wait at a bar until you call us to say you need collecting."

Abed and Troy had got up and started to walk over. "We've got it all planned," Troy said.

Abed nodded. "Operation 'Annie's Date' is a go."

"Aaaww, you guys!" Annie's face practically melted with happiness.

"I have a hashtag and everything," Troy grinned.

XXXXXX

 _Le Relais des Arts,_ 6:58PM

Annie was feeling increasingly nervous as she approached the restaurant. She had of course researched the heck out of this place as soon as she'd got home, and the reviews she found - dominated by phrases such as 'uncompromising standards', 'artisanal ingredients', 'cordon bleu trained chef' and her favorite, 'sophisticated but eclectic wine list' _,_ all said one thing - horrifically expensive and achingly fashionable. _Okay so that's two things,_ Annie corrected herself testily while also acknowledging that neither of them were a large enough part of her life for her to be comfortable with them.

She had in fact been sufficiently intimidated by what she'd read that she'd abandoned her plan to turn up in jeans and a T-shirt as an act of token rebellion to Jeff's 'hot dress' condition and had instead put on the stylish but relatively modest knee length green dress she'd bought for Troy and Shirley's graduation ceremony and had been intending to keep safe until her own graduation in nine month's time. _If he says it's not good enough I'm turning around and leaving -_ thus fortified with a sudden surge of defiance, Annie lifted her chin up, stepped forward and walked through the door.

"May I help you?" The speaker was an impeccably dressed middle aged man holding a folder of some sort. It may have been Annie's nerves talking, but she would have sworn she could pick up a hint of 'shouldn't you be at home, little girl?' in his voice.

Annie drew on her feelings of defiance and looked him in the eye. "I'm here to meet someone, Mr Winger?"

The man's expression changed to welcoming, even deferential, in an instant. "Of course ma'mselle, if you'd like to follow me?"

 _How much money do you spend here that the Maitre d' grovels at the mere mention of your name, Jeff?_

The bar was only a few paces away and Jeff, who had been chatting easily with the barman while he waited, turned to greet her with a smile spreading across his face as the maitre d' politely relieved her of her coat. Annie barely had time to register his appearance - groomed to perfection, collarless shirt under a jacket that fit so well she would have bet it was made to measure and designer chinos - before he was closing in to kiss her on the cheek, a hand resting lightly on her hip to draw her in as he did so.

"Annie, you look amazing," he said, a soft smile on his face. "I'm glad you made it."

Annie smiled back, relief at having _that_ question answered combined with relief that the lighting was sufficiently subdued he wouldn't have seen her blush slightly.

"Can I get you a drink?" He asked.

"Appletini please," she asked with a bright smile on her face. She could have sworn she saw him shudder slightly, but he didn't say anything as he turned to the bar.

XXXXXX

Jeff had arrived ten minutes early. Based on what he had observed so far, he was confident Annie would be on time and did not want to risk her changing her mind if he wasn't there when she arrived. And besides, it gave him time to order a brandy (out of deference to the establishment he forewent his usual Scotch) and good naturedly pump the barman for gossip - he had brought enough clients here on expense-account dinners that the staff knew him by name and were encouraging of his free spending habits.

He had been listening with interest to a story about a senior partner with a rival firm having a very intimate evening with a lady clearly not his wife when he heard his name being mentioned behind him. He gave his apologies to the barman and turned, seeing Annie in the process of handing over her coat.

He smiled as he watched - _she clearly decided to go for smart rather than hot, but still -_ "Annie, you look amazing, I'm glad you made it." He said as he closed in to kiss her on her cheek and noting her relieved smile as he pulled away - she'd clearly been worried about how he'd react.

Then he asked her what she wanted to drink, and she'd asked for _that_ bilious concoction - _it's early days yet,_ he thought to himself as he turned to the barman, only to see a frown on the man's face as he looked over to the Maitre d'. Jeff turned, saw the other man apologetically ask Annie a question which got her reaching into her purse and fetching out a card. The Maitre d' thanked her and nodded to the barman, who smiled apologetically and started mixing the cocktail.

 _You carded my date?_ Jeff had to fight to hold down his temper at what had just happened. _Okay, not a good start but it doesn't have to mean anything._ Instead, he pasted his smile back on his face as he handed Annie her drink and asked the Maitre d' to show them to their table.

He allowed himself a brief moment of concern as they took their seats and he saw Annie was clearly a bag of nerves as she looked around the restaurant - _well, I do look damn good,_ he thought complacently - so to relax her he launched into a mildly self deprecating anecdote about an argument he'd had at the gym that morning. _Women like guys who can laugh at themselves, it lowers their guard…_

XXXXXX

Annie was starting to think this evening had been a big mistake - oh, she'd been flattered at the handsome and well-dressed lawyer's interest in her, even though she strongly suspected she hadn't been the first woman ( _or the hundredth,_ a sarcastic voice that sounded oddly like Britta's said in the back of her head) to receive such attention.

After all, firstly she'd been carded, then, as she walked to the table she had been sure she'd heard whispered comments from a table of women clad in visibly expensive designer wear mocking her outfit - _some of us have to buy our own clothes!_ she thought to herself as she glared at them.

Then they'd sat down and Jeff had launched into an (amusing, to be fair) anecdote the main purpose of which appeared to be to boast about living in an apartment block so exclusive it had it's own private gym. Then the menus had arrived, with all the meals listed in French without a translation - _they obviously don't expect the sort of people who can afford to eat here to need one -_ attached. She had scanned the menu and eventually ordered a Filet Americain ("prepared with prime Colorado beef, free range eggs and locally sourced vegetables"), thinking she couldn't go too far wrong with a steak, while Jeff ordered a Coq au Vin. Then the food had arrived and the appalled expression on her face at seeing what looked like a - beautifully presented, admittedly - pile of raw hamburger meat on her plate must have been so obvious that Jeff had told the waiter he'd served them the wrong dishes and asked him to swap. Annie smiled gratefully at him as she started to tuck into the delicious chicken dish.

XXXXXX

Jeff could feel the date was going wrong, but he wasn't sure why. Oh, there'd been the carding debacle and then the fiasco over the food - Jeff did his valiant best to pretend he was enjoying eating raw beef blended with raw eggs, but it wasn't something he would have ordered for himself (as indeed he hadn't). Somewhere along the way though the intense, focussed, take-no-prisoners girl who had so intrigued him over the last week - _if she's as much of a driven perfectionist in bed as she is in a meeting then sex is going to be spectacular,_ as he'd thought more than once - had been replaced by a timid naïf who just seemed to be overwhelmed by the whole experience. In fact, she'd looked so frightened that he'd gone easy on his plan to charm/seduce her and instead was concentrating on ensuring she relaxed and didn't panic.

In fact the only times she'd seemed to come alive were when he'd encouraged her to tell him about life at Greendale and she'd responded with a string of scarcely believable anecdotes (the paintball war that almost saw the students mutiny after the dean rigged it for a staff member to win so he wouldn't have to give out a prize; the Halloween party that had ended in mass food poisoning because he'd tried to save money by sourcing from somebody who appeared to get their supplies from supermarket bins; the time Troy and Abed had fallen out over a blanket fort and Troy had joined the air conditioning repair school in a fit of temper, disappearing until he returned six weeks later, having led a coup against the school's leadership…)

"And this is really the first time you've been sued?" Jeff responded with incredulity.

"I know, amazing isn't it?" she said with an excited smile.

It'd work for a while, but then something would happen and she would retreat back into herself again.

XXXXXX

Annie found herself wondering when the 'important and desirable' part of the evening was going to start. Jeff appeared to have adopted the strategy of treating her as a business contact or a friend at best – _did the sight of me being carded upset him? –_ telling amusing anecdotes that seemed designed to showcase how important and successful he was while encouraging her to tell stories about Greendale that he could use as evidence to solicit for more business. He _did_ have a way of looking at her while she talked that made it hard to stay cynical though.

But still, there was a part of her that wondered what she was doing there. Jeff's stories included politicians, judges and senior business people while hers included… Troy, Abed and the dean. She had been telling him the story of the pillow fort war and Troy's exile over dessert when a well-groomed man walked over to the table, greeted Jeff effusively and talked for a couple of minutes before returning to his own table.

"I got his underage son off a DUI charge without the media finding out," he explained.

"Aren't you a bit senior to be doing teenage drinking cases Jeff?" Annie had sounded puzzled.

He shrugged. "In my line of work the gratitude of a state senator is always a useful thing to have," he took a sip of his wine. "Sorry, you were saying?"

Annie's eyes flicked over to where the senator had been standing. "No, I'd finished." _I'm a twenty two year old senior year student at a community college, what on earth am I doing here?_ Her mood darkened slightly as she remembered what Britta had said – _you'll never be Miss Right, at most you'll be Miss Right Now. Is that what I'm doing here? He thinks I'm an easy -_

"Excuse me?" The women who Annie was convinced had been sneering at her earlier that evening were getting ready to leave, and one of them had come over. "I just wanted to say how _brave_ it was of you to wear something cheap and off the peg to a restaurant like this. It's so refreshing when the younger generation refuse to be hidebound by convention."

Annie was temporarily speechless with shock as the blood drained from her face.

"Hello Jeffrey," she said as though she'd just seen Jeff. "Trading down, I see?"

"I'm sorry, do I know you?" Jeff forced out through gritted teeth.

The woman's face went grim. "New Year 2012, the Paradigm Club." She spat out. "You said you'd call, you didn't."

Jeff's memory flashed back to a heaving nightclub, a drunken make-out session and a swap of phone numbers. He briefly tried to dig up a name before deciding it wasn't important. "Then it really can't have been very memorable. Now if you'll excuse me, Clarissa-"

"Melissa!"

"Whatever. I'm with somebody who's worthy of my time. Goodbye." Jeff ostentatiously turned away as the strange woman - Melissa - turned pale and Annie glared at her. She looked as though she wanted to say something else but it wouldn't come, so instead she pivoted on a heel and walked back to her friends.

XXXXXX

That was pretty much the last straw for Jeff. He'd been on dates that were amazing and dates that had been disastrous, but this one had just been _stressful –_ he signalled for the waiter to fetch the bill and as he did so he saw Annie's expression change from defiant to something small and sad and felt his heart break slightly.

"Don't listen to her," he said gruffly. "She's just jealous."

"Of what, Jeff?" Annie's voice sounded defeated.

"That you look better in a hundred dollar dress from Target than she does in a thousand dollar one from Christian Dior of course," Jeff added a small smile, mostly for her sake.

Annie smiled back. "Thanks Jeff," she said quietly.

When the waiter returned with the bill Jeff fished out a gold card and settled it adding a generous tip in the process, by the end of which the Maitre d' had materialised with their coats. They walked out side by side, in silence.

"Believe it or not but I don't normally order raw meat and expect my dates to eat it," Annie said ruefully. "If I'd taken French instead of Spanish I would have known better than to expect it to be safe just because it had 'American' in the name."

Jeff said wryly. "And in retrospect I could perhaps have been more careful to pick a place that wouldn't be crawling with pushy politicians and angry exes."

"Yeah," Annie said, before she could catch herself.

"I'm sorry?" Jeff looked like he'd couldn't quite believe what he'd heard.

Annie did consider staying silent, but the nerves and frustration she'd been feeling all evening boiled over. "Did you pick this place because you wanted me to have a great time or because you wanted to show off what a great guy you are?" She blurted out.

"I'm sorry?" Jeff repeated, he still looked stunned.

"I mean, it must have been obvious from when I was carded that I was out of my depth in there and didn't know how to handle myself. A sensitive date would have stepped in, but you, nooo-" Annie's hand had joined in to add emphasis to her words and her eyes were on fire "-you come back with story after story of how great Jeff Winger is and what amazing people he knows!"

A part of Jeff - the part that wasn't rocking back on his heels with shock, noted that for the first time that night he was seeing the passionate, driven Annie that he had been so determined to pursue. The rest of him however -

"Well I'm sorry the third best restaurant in Denver wasn't what you expected!" He spat back. "Maybe next time I'll get us a table at Hooters!"

"Next time? _Next time?_ " Annie laughed sarcastically, she paused for breath as she backed away slightly. "You know what? This has been a real learning experience. See you around Jeff." She pivoted on her heel and stormed away, reaching for her phone as she went.

Jeff watched her go. He could have sworn she threw an extra swing into her hips for his benefit. _You really are spectacularly hot when you're angry,_ he thought, awestruck, for the second time that day.

XXXXXX

 _Is this the end? will MR WINGER retire to a monastery to contemplate the futility of his existence? Will MISS EDISON forswear all romantic attachment and focus exclusively on her academic endeavours? Tune in next time for another episode of "The Road Goes Ever On"..._

(Fashion note: for those interested in such things, Annie's outfit in this chapter is basically the dress she wore for Jeff's Christmas party in "Intro to Knots". Jeff's is far more stylish than anything he could afford after four years at Greendale...)


	3. Chapter 3

_Previously on "The Road Goes Ever On"._

 _MR WINGER, a dashingly handsome cad with a dubious moral compass has found himself captivated by the passion, energy and optimistic worldview of MISS EDISON. Through the use of a dubious stratagem that took advantage of her competitive nature he has inveigled her to accompany him to dinner at an establishment of his choosing. Tune in to this week's episode to see how events unfold…_

XXXXXX

(Apartment 303, the next morning)

Abed woke up, stretched, listened for a moment to the sound of Troy's breathing in the top bunk, then pulled on a robe and walked out of the room they shared into the main room of the apartment.

"Breakfast is on the counter," Annie said. She was sitting on the couch with a bowl on her lap, her face did not shift from the TV.

Abed looked over at the counter. At one end Britta - who had stayed the night on the couch until presumably being dislodged by Annie - was nursing a coffee. At the other, a box of fruit loops was lying on it's side next to a half empty container of three day old milk. _Still unhappy,_ Abed thought laconically.

"Is she ready to talk yet?" Abed asked Britta - when they'd collected Annie the night before, questions as to how her date went had been greeted with a furious glare, a harsh cry of _Men!_ And a frosty silence that had lasted all the way back.

"No," Britta said. "On the other hand since waking up she's fast-forwarded through _First Wives Club, 9 to 5,_ and is now on _Thelma and Louise._ "

Abed frowned fractionally. "Female revenge movies are not Annie's trope. We have to break her out of this, I need her help if I'm going to use Jeff's car in my film."

Britta looked slightly shocked. "Seriously, Abed?"

Abed ignored her objections. "You have to talk to Jeff-"

" _WHAT?"_ Annie screamed - she'd obviously overheard.

 _Now you've done it,_ Britta glared at Abed as the petite brunette got up and stormed over.

" _NOBODY_ is talking to him!" Annie screeched. Abed abstractedly wondered if the bats that lived in the roof of their building had taken flight yet.

Annie paused for breath before letting fly with another volley. "Not that you'd get a word in edgeways anyway! He won't listen to anything you've got to say because he'd be too busy telling you how hot and smart and funny he thinks he is! That's if he isn't too busy showing off his perfect hair and ridiculously defined-"

Annie stopped talking suddenly as she took in the expressions on Britta's and Abed's faces (well, mostly Britta's) and realised she was on the verge of saying too much.

"Was it really that bad Annie?" Britta said.

Her friend looked like she was about to explode again. Instead, she deflated slightly. "Was it really so unreasonable of me to hope for a nice evening with a cute guy who would go out of his way to make me feel special?" she said sadly. "Instead I got -" her voice got deeper as though impersonating a man "- look at me! You know you want to! I'm so rich and busy and well connected! I buy fancy clothes that show off my flawless figure and spend more on hair product than you do on rent! Looking that good doesn't come cheap you know!" Annie dropped back into her own voice for that last sentence - she didn't seem to notice, but the looks Abed and Britta exchanged showed they did.

"I'm sure he's learned his lesson," Abed said. "Next time-"

"Next time? _NEXT TIME?_ " Annie's voice once again rose to a level only bats or dolphins could hear. "I'd sooner date _Starburns_ than go out with that, that - _popinjay_ again!" She gave another exasperated squawk, pivoted on the spot, tossing her hair as she did, and marched into her bedroom, slamming the door behind her.

"Popinjay?" Britta said.

"She's been reading Jane Austen again," Abed explained.

"Oh dear."

"I know this isn't my field," Abed added. "But she seemed to be too angry for somebody who doesn't care."

"I'll say," Britta nodded in agreement.

"Did we just have another Anniequake?" Troy had emerged, yawning.

Abed nodded. "A six point five, maybe a seven."

"Oh man, that's not good." Troy said as he joined them at the counter. "So what do we do about it?"

Abed tilted his head slightly as he thought for a moment. "We need a caper," he said eventually. "And I think I have just the thing."

"Cool!" Troy said, grinning.

"Abed, this had better not be just about getting Jeff's car for your film," Britta warned.

Abed fixed the blonde with a stare. "Of course it isn't, Britta." _We'll also never have pancakes for breakfast again if this isn't sorted out._

XXXXXX

(Outside the offices of Petrocelli and Winger, later that morning)

"-does everybody understand the plan?" Abed wrapped up.

"I don't see why we have to do it _this_ way," Britta grumbled, pulling on the hem of her dress to get it closer to her knees.

Abed sighed microscopically as he repeated himself. "You're the only one who knows Jeff so you have to go in and talk to him. Troy and I will be distracting the receptionist for you by saying we're there to service the air conditioning-" they were both wearing workmen's overalls and carrying toolboxes "-but you have to get past the security guard yourself."

"You're a cute white girl dressed formally," Troy added. "Nobody's going to question why you're in a building like that."

Britta gasped with shock. "Troy, that's sexist _and_ racist! There's no reason why you couldn't-"

Troy cut her off. "Get real Britta - if Osama and Obama here-" he gestured to Abed and himself "-are caught wandering around places they shouldn't be we'll get taken to jail, if you get caught you'll get taken to dinner."

"Dinner with sleazy lawyers isn't all it's cracked up to be you know - I've been in jail cells that were better!" Britta huffed, but she pivoted on the spot, blonde hair swishing around her shoulders, and started striding purposefully towards the door of the building, heels clicking defiantly on the concrete sidewalk.

Troy's eyes were suddenly fixated on her hips. "Aren't we-" he said dreamily.

"Supposed to go in first?" Abed said, sounding equally distracted. They looked at each other, the spell was broken and they scrambled to get through the door first.

XXXXXX

(Jeff Winger's office)

"Jeff, we need to talk!" Britta said sternly as she marched into his office. "Alone," she added, glaring at the statuesque, auburn haired young woman in a black pencil skirt, crisp white blouse and killer heels bending over Jeff's desk and pointing at something in the document he was reading.

"It's okay Michaela," Jeff sighed. "Give us ten minutes, please?"

"Of course, Mr Winger," she said as she straightened up and sashayed out, glancing cooly at Britta as she went.

"Really, Jeff?" Britta's tone had gone cold and disapproving. _You asked my friend out on a date while you were holed up with - "_ Who's the bimbo?"

"Way to objectify women Britta," Jeff snarked. " _Michaela_ graduated Summa Cum Laude from Denver Sturm, where she was an editor of the Denver Law Review. She turned down seven job offers before accepting ours because she wanted to get in on the ground floor of a new and growing firm."

"Oh," Britta deflated somewhat. To distract attention from her embarrassment, she reached for the chair opposite Jeff and sat down.

"How did you get in anyway"? Jeff said. "You don't work here and you don't have an appointment - you shouldn't have got past the front door."

"Troy and Abed kept the receptionist distracted and your security guard's a man." Britta said the last with a tone of exquisite contempt. "I walked straight past him waving my college ID and he never looked up at it once," she crossed her legs - Jeff's eyes instinctively tracked the movement. "Yeah, like that."

 _And once you were in nobody challenged you because you look like you belong here,_ Jeff thought to himself as he unapologetically reviewed her outfit - pumps, smart dress and formal jacket. Britta met his look defiantly when it finally reached her eyes.

Jeff grinned suddenly. "You know, if you'd worn a dress more often when we were seeing each other we might have lasted longer."

"Why? Would it have stopped you from being an insufferable jerkass?"

 _Ouch._ "While I'd happily sit here flirting with you all day," Jeff said dryly. "I'm very busy and I doubt that's why you came anyway, so why don't you get to the point?"

Britta decided to take him at his word. "What did you do to Annie? She's been furious and refuses to talk to anybody about anything other than what a monster you are since we collected her last night."

Jeff's mood changed at a stroke. "What did _I_ do to _her_ \- oh, let's see-" he sat up straight in his seat, his face pale as he sarcastically began counting items off on his fingers. "One - I took her to one of the most exclusive restaurants in Denver, where you normally have to book a month in advance. Two - I covered for her when she realised she'd ordered raw beef by mistake by giving her my meal and eating the disgusting mess myself. Three - I defended her when a jealous bitch of an ex tried to belittle her outfit and tell her she didn't belong there. And four -" Jeff held up his hand with the fingers extended and thumb tucked into the palm "-when it was clear at the end of the night that something was wrong I tried to take the blame for it so she'd feel better. And in return, the ungrateful little-" Jeff paused for breath "-went berserk, accused me of only wanting to show off and stormed off into the darkness vowing never to see me again!"

"It's always somebody else's fault with you, isn't it Jeff?" Britta didn't look impressed.

Jeff's face went flat and hostile. "I'd like to say it was great Britta, but - I'm sure you can find your own way out."

Britta ignored him. "Why did you go to so much trouble and effort to ask Annie out?" She said instead.

"What?"

"Humour me, Jeff." Britta still showed no sign of moving.

"I _can_ call security you know."

She looked completely unimpressed. "I'll bite and I'll scream, you know it – and don't change the subject!" She'd seen Jeff raise an eyebrow and start to form a grin.

Jeff looked like he was tempted to argue, but eventually thought better of it. Instead he just shrugged. "She's smart and uncynical to a fault with a driven energy that promises great things –"

"Ew, gross!" Britta turned her nose up in disdain.

Jeff smirked. "You _did_ ask. And there's a fresh naturalness about her that other women spend fortunes trying to achieve -." Jeff no longer seemed to be talking to Britta, instead he was smiling softly as he looked over her shoulder.

 _He isn't looking at me anymore, he's lost in dreamland!_ Britta realised with disbelief. "So what's changed then?" She blurted out to stop his stream of consciousness Annie-centred musings.

Jeff seemed to shake himself back into the real world. "Well she's nuts obviously, and she hates me-"

"No, I meant what's changed with you?"

" _What?"_

 _I'm so glad there's no Hell, because if there was I'd definitely be going there for this,_ Britta thought to herself as she gathered her thoughts and locked her conscience away in a small, dark room. "I mean, when did Jeff Winger suddenly decide to give up on a girl he liked after an initial setback? One of your less attractive qualities has always been your refusal to take 'screw you' as an answer."

Jeff stood up, gaping in disbelief. "Are you really asking me to chase after your friend? Really, Britta? I thought you'd be buying champagne!"

 _If it was up to me, I would - but you don't know what it's like to be steamrollered by Abed,_ she thought to herself. "Annie was really looking forward to last night, you know?" She said instead. "She's had a pretty crappy dating history-" Britta swiftly outlined the gay high school boyfriend, Vaughn, Dr Rich and 'Clint Hightower', though she didn't mention Troy "-and thought she was overdue a nice evening with a cute guy who would treat her special. And for some reason she thought you could be that guy. As I said, she doesn't have much experience with men." She finished dryly.

Jeff had listened to Britta's tale with growing concern (and had taken notes during the catfishing portion) and a growing sense of realisation that what to him had meant to be nothing much more than a fun evening with a cute girl had been something else to her. _I was after a good time, she was after some sort of reaffirmation of her worth as a dating prospect, instead -_ Jeff wasn't good at self-analysis, and even less so at self-criticism, but he wasn't a stupid man and there was a part of him that liked what he'd seen in Annie and felt some responsibility. So -

"What do you expect me to do, Britta? I doubt she'd listen if I asked her out again," he sighed.

"I'm not asking you to ask her out again Jeff, just come up with something to make it okay. Isn't telling people lies they want to hear the job you're so good at, after all?"

"Telling people lies they want to hear at three hundred bucks an hour is the job I'm good at, Britta." He snarked back at her. "I'll try and think of something," he sighed in response to her glare.

"Good - but do it fast please, I need to get Abed off my back."

Jeff looked confused again. "Abed? What's he got to do with this?"

Britta rolled her eyes. "He needs a fancy car for a scene in a movie he's making as his degree project and he wants yours. He was hoping Annie would persuade you to let him borrow it."

"Abed wants to put me and my car in a movie?" Jeff abruptly sat upright in his seat, looking intrigued.

 _No, he only wants your car - he's not interested in you,_ Britta thought. But she bit off her first reply as she realised Jeff's vanity had just been engaged. "Yes, but I suppose it's unlikely to happen now." Acting on a hunch, she picked up her bag and stood up. "Thanks for your time Jeff, and I'll see you around." She waved to acknowledge his distracted goodbye and slipped out, leaving him alone with his ego.

XXXXXX

It was the end of the day, and if Jeff Winger had allowed himself to be distracted by his somewhat odd meeting, he didn't let it show. He hadn't stopped chewing over what Britta had said and, almost on a whim, he called up the records of the Greendale case and located the paper he was looking for - the contact details of the members of the Liaison Committee. He dialled a number into his phone, it rang five times before being picked up.

"Is that Abed Nadir? This is Jeff Winger - I think we may be in a position to do each other a favour…"

XXXXXX

 _Is this the end? will MR WINGER retire to a monastery to contemplate the futility of his existence? Will MISS EDISON forswear all romantic attachment and focus exclusively on her academic endeavours? Tune in at the same time next week for another episode of "The Road Goes Ever on"..._

 _(Fashion note: for those interested in such things, Annie's outfit in this chapter is basically the dress she wore for Jeff's Christmas party in "Intro to Knots". Jeff's is far more stylish than anything he could afford after four years at Greendale...)_


	4. Chapter 4

_Previously on "The Road Goes Ever On"._

 _MR NADIR, a chessmaster with plans of his own, MR BARNES, a good-hearted simpleton, and MISS PERRY, a lady of easy virtue, on seeing the distress their friend MISS EDISON was suffering concocted a plan to make MR WINGER approach MISS EDISON in a more constructive manner. Tune in to this week's episode to see how events unfold…_

XXXXXX

(Mulligan's Irish bar)

"Girls!" Britta said, holding her beer bottle in front of her.

"Girls!" Annie and Shirley returned the toast, clanking their own drinks - an appletini and a Virgin Mary respectively - against hers. Britta had been feeling vaguely guilty about going along with Abed's plan to get Jeff and Annie talking again and had decided to organise a Girl's Night to cheer her friend up. A few phone calls later and they'd all agreed to meet on Friday in Greendale's only Irish-themed bar. There was a more cynical motive of course - Britta still hadn't had Annie's version of how the date went and was desperate to compare it to Jeff's and was hoping a few drinks would loosen the younger woman's tongue.

 _Not just yet though, she needs to be softened up first._ Instead she turned to her other friend. "Any news Shirley?"

"I saw my lawyer yesterday," she said with a sad smile on her face. "He thinks he can get me to see Elijah, Jordan and Benjamin every other weekend instead of once a month."

Britta nodded sympathetically. "It sucks that getting back together with Andre didn't work out, but it's his fault that he couldn't cope with you becoming a strong, independent woman who didn't need a man to keep her," she added firmly.

Shirley was silent for a moment as though not sure as to whether she should be offended at becoming a feminist role model before accepting Britta's words in the spirit they were meant. "Thank you, Brit-ta," she said slowly. "It was my duty to do everything I could to try and save my marriage, and I'll never regret having Benjamin." She added bravely.

"Aaaww," Annie hummed sympathetically. "You need a better lawyer Shirley," she added supportively.

"He's the best I can afford, you know my shop is barely breaking even as is." Shirley sat up suddenly, her sad expression replaced by a fixed glare pinning Annie to her seat. "Speaking of lawyers - we still haven't had the run-down on your date, missy."

Annie spluttered into her drink. "Shirley!"

Her friend was unmoved. "It's early and we've got all night Annie."

Annie sighed and took a sip of her drink. In truth, she'd reached the stage of wanting to talk it out but had spent so much time rebuffing her friends' attempts to talk to her she'd been slightly afraid to. She therefore seized the opportunity with both hands and proceeded to unburden herself.

"...so then we we were finally leaving the restaurant," it was two drinks later and Annie was winding up her monologue. "And even Jerk McPointyface had started to notice how terrible it had been, so he apologised for being too awesome for me and said we should have gone to Hooters instead!" Annie was sitting bolt upright now. "So I told him what I thought about him and stormed off without looking back."

"You go girl," Britta said, holding up her hand for a high five. Annie gave it a firm slap.

Shirley didn't attempt to join in. "Yes, I can see how terrible it must have been - a rich, successful, good looking and smartly dressed man wants to spend his money on treating you. It must have been a complete nightmare." Her judgemental tone of voice was out in full force.

Annie squeaked with shock at this response. Before she could say anything, Shirley started talking again.

"At least one good thing came of it though."

"What, Shirley?" Britta said - Annie was still too speechless to reply.

"You two have been developing something of a habit of recycling each other's exes-" Shirley kept talking over the outraged cries of the other two "-first there was that shirtless freak you ran off to Delaware with-"

"Vaughn," Britta and Annie mumbled at the same time.

"Then there was poor Troy-"

"He seemed okay with it," Britta mumbled.

Shirley ignored her. "And now this Jeff guy. It's probably just as well you ended it now before you start keeping joint schedules."

"That's not fair, Shirley!" Annie had finally found her voice. "Britta has slept with dozens of guys I wouldn't go near! Sorry Britta," she gave her friend an embarrassed smile.

"Gee, thanks girlfriend." Britta mumbled. Then more loudly - "and Annie's hardly slept with anybody! Sleeping with all her exes doesn't prove anything!"

Now it was Annie's turn to look offended. "And Jeff doesn't prove anything either! He's a guy any girl would be curious to-" Annie's mouth slammed shut as she realised what she was about to say.

"Huuuh-hmmm," Shirley hummed meaningfully.

XXXXXX

(Apartment 303 - early the next day)

Annie yawned and smiled apologetically over her coffee at Abed and Troy. "What time's the rental car due again?" She asked. Two days ago Abed had told her that with the collapse of Plan A - get Annie to lure Jeff into lending Abed his car - he'd activated Plan B - rent a car ("not one as cinematic as Jeff's") for the following weekend, paying extra to have it delivered to the apartment. He'd also suggested the three roommates could take a road trip into the mountains, spend a morning shooting driving footage then have a picnic - Annie had recognised an attempt by her friends to cheer her up and had spontaneously hugged a somewhat bemused Abed.

"Half past six," Abed said.

Annie looked at her phone - 6:37. "It's la-"

She was interrupted by Abed's phone vibrating. "That's the car," he said. "Let's go."

Annie threw down the last of her coffee, picked up the picnic basket and followed the boys out of the door.

XXXXXX

After she'd met Jeff for the first time and been baffled by why the guys had been so impressed by his car, Annie had attacked this gap in her knowledge with her usual determination. She'd watched a whole host of Youtube videos (many of which for some reason were presented by an oafish Englishman who somehow had millions of hits), so she no longer needed to be told why a Ferrari California was a nice car. Even if she had done none of that research however she would still have recognised it thanks to the jerkass male model-type leaning against it in his designer casual gear and sunglasses.

"Hi guys," Jeff Winger smirked as they approached.

"Hi Jeff," Abed said.

"Dude!" Troy grinned.

"Abed, what the hell?" Annie gasped. _I was really looking forward to a fun day out with my friends, and they do THIS -_

"Don't blame Abed, it was my idea."

Annie pivoted to face Jeff, he was smiling as though the sight of her about to explode amused him somehow.

 _You really do look spectacularly hot when you're angry,_ he found himself thinking for the - actually, he'd lost count of the amount of times he'd thought that. "Believe it or not, but I really don't like it when cute girls are angry with me - it causes a great disturbance in The Force," he said instead, causing Abed to perk up suddenly in the background.

"So when I found out Abed was making a movie and wanted to use my car," Jeff continued, "I thought I'd never been in a movie before and it sounded like fun, and if seeing me help out your friends meant you'd stop using a picture of me as a dartboard then all the better."

"I don't have a picture of you," Annie huffed.

"Do you want one?"

Jeff was openly smiling now, a big aren't-I-the-cutest-thing-you've-ever-seen smile. Annie desperately wanted to stay angry with him, but found herself snorting with exasperated amusement instead.

"Fine!" She threw up her arms in defeat. "We'll use your car." She turned to face Troy and Abed who, on seeing the confrontation wind down, had started towards the trunk with the bags.

"You'd think a car that cost so much would have a decent sized trunk," she grumbled as she helped load the car - Annie was determined not to surrender with too much grace.

"People who can afford to drive cars like this can afford to have their luggage shipped," Jeff said blandly. He'd moved so that he was standing next to her, almost but not quite close enough for their shoulders to be touching - close enough for Annie to smell his cologne, which like everything else about him seemed to be both effortlessly expensive and perfectly judged to make a positive impression.

XXXXXX

Then there was the discussion over seats…

"I think Troy should sit in the front," Annie said. There's hardly any leg room in the back and he's the biggest of us."

"No!" Jeff yelped as Troy moved towards the front of the car, the others turned to look at him in surprise just as he composed himself.

"This is an Italian sportscar Troy," Jeff said in his best 'you're about to make the most important decision of your life, listen to me and it'll be the right one' voice.

"Yeeeess, Jeff?" Troy looked confused.

"There's a special sensor in it. If anybody other than a hot girl sits in the passenger seat, it ejects them." Jeff looked deadly serious.

"That can't be true, can it?" Troy looked even more uncertain.

"Think about it Troy," Jeff had walked around the car and was now facing him. He gripped his arm, man to man, to add sincerity to his words. "All the times you've seen a car like this - magazines, movies, TV - how often was there a guy in the passenger seat?"

Troy's face lit up as though something previously obscure had become clear. "Pretty much... none?" He said.

Jeff patted his elbow approvingly. "Now you know why, buddy." He said.

Troy nodded decisively. "Annie - you ride upfront," he said as he climbed into the back.

"That was cruel Jeff," Annie murmured as she moved towards him. The force of the criticism was somewhat muted by the smile she was fighting to keep off her face however.

As she opened the car door however her smile was replaced by a puzzled frown. "What's this?" She said, picking up a small box.

"It's on the passenger seat and you're the passenger - it must be yours," Jeff said casually as he eased himself into the driver's seat.

Still puzzled, Annie slid into the seat and opened the box. Inside was a simple white lily, with a silk bow and a pin attached. There was also a card, Annie took it out and read it. The message was straightforward enough -

 _Peace offering? JW_

Annie didn't say anything, the smile on her face as she pinned the corsage on her dress was answer enough for Jeff.

"Buckle up everyone, we're on our way." He said.

"Road trip!" Troy and Abed yelled simultaneously.

XXXXXX

As they drove around the edge of the Denver metropolitan area and into the rising sun, Jeff cheerfully explained the deal he'd reached with Abed - there was a racetrack an hour's drive away that was having an open day, he'd spend the morning taking the guys round the track and allowing Abed to take footage and sound recordings of the car going flat out before they'd drive back along country roads to allow him to take footage from the side of the road. The journey there had it's diversions however.

("Look at Jeff and smile at him Annie," Abed said.

"Why, Abed?"

"I need some reaction shots. We can decide what you're reacting to later."

So she turned, looked at Jeff and pasted a smile on her face. Either not knowing she was supposed to be acting or not caring, he smiled back. Annie decided she liked his smile.

"That's the look I need," Abed said.)

However, the attempt to play games didn't go so well.

("I spy with my little eye something beginning with 'S'."

"Sky, Troy."

"How did you get it so quickly, Jeff?"

"What else is there, buddy?"

Troy looked out over the flat, empty plains of eastern Colorado. "Oh yeah," he said sadly.)

They got to the racetrack in time for the safety briefing, only for the boys to disappear with their camera and sound equipment while Jeff was checking out safety helmets.

"They ran off to get B-roll of the track and parked cars," Annie said apologetically.

"Then you're up first," Jeff said with a grin. "You'll need this," he tossed her a helmet.

XXXXXX

Sitting in the passenger seat of Jeff's car on the starting line, listening to the gathering roar of engines around her as the starting clock counted down, Annie decided she'd never been so terrified in her life. She watched nervously as Jeff stood on both the gas pedal and the brake at the same time and hit a button on the dashboard. She felt the car start to vibrate as the engine started to give her some hint of just what four hundred and eighty horsepower meant.

"There's one statistic you really need to remember with this car Annie," Jeff's grin was wolfish.

"Yes?" Annie managed to squeak.

"Zero to sixty in three and a half seconds." The countdown ended, Jeff released the brake and Annie was abruptly slammed into her seat as the launch control hurled the car forward. By the time it reached the first bend, Annie was screaming - whether out of fear or exhilaration she wasn't sure - and it felt like she barely stopped before the car finally took the chequered flag.

"I've never been so scared in all my life," she eventually managed to say when the car rolled to a halt in the paddock.

"In a good way or a bad way?" Jeff grinned at her.

Annie rolled her eyes. "Help me out please - I don't think I can stand."

Jeff jogged around the car, offered her his hand and helped her out of the car. When her knees gave way as she tried to stand, his arm slipped smoothly round her waist to hold her up.

She smiled and blushed as he caught her, and then her smile faded slightly. _How many times have you done this before, Jeff?_ Then she shrugged, decided she wasn't going to care if this was a regular thing and would simply enjoy allowing him to support her until her legs were ready to.

XXXXXX

"Not that this isn't the coolest day out _ever_ -" Troy was loaded down with a track branded baseball cap, scarf and a giant foam hand, his one free hand was holding a colossal hot dog he'd bought from a concession stand. The guys were walking back to where the cars were coming to a halt as they left the track. "But why are we doing this, Abed? You haven't decided what sort of movie you're making yet and you've never mentioned wanting to make a road movie."

"When was the last time we had pancakes for breakfast?" Abed said.

Troy's forehead wrinkled in confusion at the apparent non-sequitur.

"Eerrrm… four weeks ago when we stopped at IHOP on the way back from the midnight showing of the _Rocky Horror Picture Show_?" Troy grinned suddenly as he remembered that night. "You were the coolest Frank, dude!"

Abed's eyes widened slightly in surprise. "When we was the last time we ate homemade pancakes for breakfast? At home?" he amended.

Troy's puzzled expression returned. "Was it… before Annie found out she was being catfished?"

Abed nodded in approval. "That's right. She hasn't looked at another guy since, and she hasn't made pancakes."

"I don't get the connection, buddy." Troy was still looking confused.

"She flicked her hair and giggled when Jeff complimented her on her filing that first day he was at Greendale. It's the first time she's done that for a guy since Rich."

"Oooh," understanding was dawning across Troy's face. "You think if we hook her up with Jeff she'll start making pancakes again? And be happy," he added, almost as an afterthought.

"For breakfast, Troy." Abed said firmly.

"For bre- damn, but he's moving fast!" Troy's response was interrupted by the sight of Jeff helping Annie out of the car and slipping an arm around her waist as she smiled up at him. They walked a couple of paces like that then Annie slipped out from under Jeff's arm when she saw the boys and waved to attract their attention.

"How was your race Annie?" Abed said as the two groups closed up on each other.

"It was terrifying - you've got to do it!" Annie was practically vibrating with adrenaline aftershock.

Jeff smiled indulgently as he watched her excitement. "Okay, who's next?" he said.

XXXXXX

 _It's actually been a good day,_ Jeff thought to himself as the Ferrari drove into the sunset on the way home. He'd kept his promise to give Abed and Troy runs round the track - Abed had almost frozen solid with fear, but Troy whooped with glee all the way round and high fived Jeff at the end (admittedly, he only got in the car after Jeff apologised for the joke about the hot girl sensor). They'd had Annie's picnic lunch at the track and then driven even further east to get the road footage Abed wanted and then had dinner at a roadside diner that billed itself as the last chance to stop for fuel and refreshments before Kansas. The sun was already touching the horizon as they started back, and now as it got dark and the car's headlights came on Jeff was the only one still awake, alone with his thoughts.

They went in some decidedly diverse directions. _Are they a couple?_ He thought as he glanced in the rear view mirror and saw Abed's head resting on Troy's shoulder. _I've known gay couples who've been together twenty years who are less in sync than those guys._ Reluctantly he discarded that idea - well though it fit, Jeff was sure Britta would never have been able to keep that a secret, especially during the periods she was sleeping with Troy. For the same reason, he discarded the idea that there was some strange triad thing going on with Annie, for all that they lived under the same roof and seemed to do almost everything together.

 _Maybe I just really want to believe she's single,_ he thought to himself - Jeff was a sufficiently experienced lawyer to know that you should check extra hard when the evidence seemed to confirm your wishes, but he discarded that thought when he recalled the guys seemed to be happy that he was interested in Annie and were supportive of him chasing her. _Unless they really are gay after all, and want some of the Winger action for themselves and are using her to reel me in,_ he chuckled to himself at the thought.

"Wazzup?" Annie had stirred at the noise, Jeff turned to look at her only to smile softly at the sight of her already drifting back to sleep.

But most of all, as the car ate up the miles heading west and as twilight gave way to night which in turn gave way to the lights of Denver on the horizon, Jeff found his thoughts coming back to the girl in the passenger seat. He realised suddenly that in the brief time he'd known her he'd seen her angry, he'd seen her stressed, he'd seen her focussed and passionate, he'd even seen her laugh, but he'd never seen her relax or simply be happy. Now as he glanced at her in the corner of his eye, stretched full length into the footwell, hands crossed on her lap and her head resting peacefully on her shoulder with a small smile on her lips as she dreamt of something that amused her, he realised he could tick the first of those two outstanding states off his list. _Who are you Annie Edison, what does it take to make you happy?_ He thought suddenly.

As his mind wandered down these pathways, he found himself increasingly rueing the lost opportunity their failed date represented. _I know you better now,_ he thought as once again he recalled the day just past spending time with her (and her friends, tell nobody but he didn't hate the time spent with Troy and Abed either) doing uncomplicated, fun things that had nothing to do with gaining advantage over a rival or wooing a contact. He was pretty confident she'd enjoyed herself too - _I guess I'm even awesome at not going out of my way to be awesome,_ he thought to himself with a smirk as he came to a decision. _I want to try again. Will you let me?_

XXXXXX

"We're back guys," Jeff announced as they got back to their starting point.

A combination of a late night, an early start, a busy day, a big meal and straight, empty roads had sent Annie to sleep almost immediately after leaving the diner. She mumbled an apology followed by a thank you to Jeff as she stirred awake and stretched - she blushed slightly as she saw the way he looked at her while she did, but she couldn't help the hint of a warm glow inside. _Okay, so maybe there's a little more to you than a self-obsessed jerk who's a bit too aware of how good looking he is,_ she thought with an inward smile as she remembered the day they'd had - in particular his patience with Troy and Abed's antics (with one exception - the giant foam rubber hand had been stuffed into a trash bin when Troy attempted to tie it to the trunk of the car), something which was very rare among people who hadn't known them for a very long time. It was - conditionally at least - a good point in Annie's book.

Troy and Abed had already clambered out of the back of the car as Annie rather more sedately exited and were gathering their things from the trunk as Jeff walked around and joined her.

"Thanks for letting me do this," he said quietly. "You would have had every right to tell me to pound sand after the other night."

"I did it for Abed," the small smile on Annie's face belied her words somewhat. "He would never have forgiven me if I'd cost him his chance to-"

"That's everything," Abed interrupted as he and Troy closed the trunk and stood up to face them. "Do you want to stay the night, Jeff? It's getting late and our couch is comfortable."

Jeff smiled. "Thanks Abed - I don't think I want to risk leaving my car parked on the street overnight in this neighbourhood though."

Abed tilted his head as though considering this, then nodded once. "We'll get our things inside. It's been a good day, Jeff."

"Thanks dude - awesome car! See you next time," Troy said as he offered Jeff a handshake. They both squeezed, squeezed a bit harder and then let go, as though satisfied with the result of the strength test.

"It's been fun Troy. Until next time buddy," Jeff replied amiably.

"Come up when you're ready Annie," Abed said as he started walking towards the door.

" _Are we leaving them alone?"_ Troy fake whispered as he followed Abed into the building.

Annie shifted nervously on her feet as she realised she was indeed alone with Jeff. He simply smiled as though he found her nervousness to be adorable.

"I really am sorry about the other night," he said after a moment. "And if it's okay with you I'd like to try a do-over."

Annie's heart leapt into her mouth as the mellow glow she'd woken up with was abruptly replaced with nervous anticipation. _He can't be, can he?_

"We had fun today, didn't we?" Jeff continued. Annie nodded, somewhat shakily.

"I'd like to show you we still can without needing your roommates along for the ride," he grinned ruefully and nodded in the direction of the door Troy and Abed had just gone through.

Annie was temporarily silent while warring thoughts clashed in her head - on the one hand, he was smiling at her in a way that made her toes tingle, but on the other - _you'd better not be thinking I'm the sort of girl who's head can be turned by a fancy car and a smooth line, Jeff. You're going to need to work harder than that to prove you're serious about this._

Instead she returned his smile, though hers was bright and assertive not soft and seductive. "That's a nice thought Jeff, but it's getting late - do you mind if I sleep on it?"

And then, because she saw no harm in very slightly giving in to temptation (though she told herself she was merely throwing him a bone), she stood up on tiptoe to give him the lightest peck on the cheek before retreating out of range before his arms could close on her. "Goodnight, Jeff," She said as she turned on the spot and, with a small wave, followed Troy and Abed into the building.

 _You little minx!_ Jeff was stunned into immobility, completely unable to take his eyes off Annie's retreating form. _I was so close, I know I was! You're going to be the death of me, Annie Edison._

XXXXXX

 _Has MISS EDISON taken the measure of the charming rake? Will MR WINGER come up with another scheme or is he now the one waiting on events? And will MR NADIR ever eat MISS EDISON's home made pancakes again? Tune in at the same time next week for another episode of "The Road Goes Ever on"..._

 _(Author' note - it has just occurred to me that I've got half way into this thing without giving due thanks to my inestimable beta reader Jeffwik, who has, as always, read every last word of every chapter and suggested countless improvements, all of which have improved and tightened up the story. Thanks Jeff!)_


	5. Chapter 5

_Previously on "The Road Goes Ever On."_

 _MR WINGER and MR NADIR colluded with each other behind the back of MISS EDISON in an effort to show a more sympathetic side of MR WINGER to her, but ending with MISS EDISON apparently taking control of events and MR WINGER gasping helplessly in her wake. Tune in to this week's episode to see how events unfold..._

XXXXXX

(The Vatican Bar, Greendale)

Jeff Winger was desperate.

He'd spent the whole of Sunday obsessing over the quirky, cute, exasperating and frustrating riddle that was Annie Edison. In fact he was so desperate that by the evening he'd hauled himself off to the bar where Britta worked to ask her for advice.

"What are you doing here Jeff"? she said as he walked through the door.

"Your customer service presentation needs work Britta," he said wryly as he sat on a stool at the bar.

" _Customers_ get a proper welcome. You - " Britta completed the sentence with a shrug, going silent as she waited for him to speak again.

"I need your advice." Jeff sighed. "About Annie."

 _That took her by surprise,_ Jeff thought with some meagre satisfaction as he saw her eyes open wide.

 _How does Abed do it?_ Britta thought as she flashed back to lunch that day with him and Troy. They'd told her about the day thay'd had and Abed had outlined that Jeff's next move would almost certainly be to reach out to Britta.

"What about Annie?" she said.

"I spent the day with her, Troy and Abed yesterday helping Abed film car scenes-" Jeff explained, not realising Britta already knew this "-and by the end we'd had fun, relaxed and she seemed to be over last week, so I asked her out again."

"Ooh! Don't tell me, let me guess-" Britta said with relish "-she blew you off?"

"Yeah," Jeff said dryly. "And I was sure she was on the verge of accepting - where am I going wrong Britta? She's driving me nuts!"

"I can't believe I'm going to do this," Britta muttered. "This is going to cost you Jeff," she said more loudly.

Jeff had played this game with her before. "Hit me with the expensive stuff," he said pointing at the top shelf. He - fairly unapologetically - allowed himself to admire the view as she stretched up on tiptoe to reach the most expensive Scotch the bar stocked. _Hey, I'm a lawyer not a saint..._

"The first thing-" Britta said as she poured a shot out into a tumbler "-is to stop looking at my ass."

"Oh please." Jeff took the tumbler from her. "We both know that's why you wear the tight jeans." As if to add emphasis, he slipped a ten dollar bill into the tip jar.

"I'm serious Jeff." Britta wasn't smiling. "Annie has self confidence issues where guys are concerned. If you spend your time eyeing up other women she's not going to be happy."

"Eyes only for her, got it." He waved his tumbler in a mock salute before taking a sip of the Scotch and nodding imperceptibly. "What else?"

"Okay, the big thing." Without asking, Britta poured herself a vodka and added it to Jeff's tab. "Annie isn't the sort of girl to respond to your usual 'look at me I'm a rich douchebag! Do you want to come back to my expensive apartment for an emotionless shag and disappear in the morning?' routine."

"Geez Britta - you remember how we met so well," he said sarcastically. A grin suddenly spread across his face. "Oh, and 'shag'? Just how much time have you been spending with Ian Duncan?"

"That's not relevant," Britta mumbled as she blushed, unable to meet his eyes. "We're supposed to be talking about _your_ private life."

"The thing to remember about Annie," she deflected hurriedly, "is that she doesn't pretend to believe in hearts and flowers, happily ever after Hallmark card romance stuff to play hard to get - she really believes in it. It's what she wants and what she deserves, and if you can't give her that then you'd be better off leaving her alone."

Jeff frowned slightly in thought.

"Because remember one thing Jeff," Britta continued, now deadly serious.

"What, Britta?"

"I know where you live. If you think you can use her and throw her away, I'll break into your apartment block and boost that fancy car of yours and sell it for spare parts. You know I can do it."

Jeff shuddered slightly as he drained his Scotch. "Give me another one," he said. "From the middle shelf."

Britta beamed a radiant smile at him.

 _Well, I have to start somewhere…_ Jeff grumbled to himself as he saw her expression.

XXXXXX

(Shirley's Snacks, Greendale Community College)

Annie tried to buy something from her friend's shop every day by way of showing support, and this Monday was no different - it did no harm that a part of her was still walking on air after the weekend and wanted somebody to gossip to. _Mr fancy Italian car and thousand dollar shoes is chasing ME - and I'm making him work for it!_ She thought as she smiled to herself - not since she'd returned from Delaware and Troy had had his "Annie's got hot" moment had she had a cute guy she liked pursue her so ardently and she was determined to enjoy the experience.

"What can I get you Annie?"

"Oh - hi Vicki." In her reverie, Annie hadn't noticed that Shirley wasn't at the counter and Vicki was manning it alone. "Is Shirley around?"

"She got a phone call and ran into the quad crying," Vicki said.

"Oh dear," Annie's face fell as she turned towards the door.

"I know, right? The lunch rush will be starting soon… hey, aren't you buying anything?" Vicki called plaintively after her.

XXXXXX

"Shirley, what is it?" Annie said softly as she approached her friend and sat down on the bench next to her. Shirley was rocking slightly, an expression of pure misery on her face and didn't acknowledge Annie's arrival until she reached out and gently touched her on the arm.

"I spoke to my lawyer," she said in a bare whisper.

 _It can't be good news if it's this quick,_ Annie thought to herself.

"He said that Andre has threatened to take the boys to Chicago to live with his cousin if I don't stop pushing for more access," Shirley said miserably, confirming Annie's premonition.

"Oh Shirley-" Annie didn't know what to say. Instead, she pulled her into a hug and held her while she cried quietly.

"My pastor says that God never gives us burdens that are too great for us to bear," Shirley said eventually. "But I couldn't bear to lose my boys Annie!" She sounded like she was about to cry again.

"Then you're not going to!" Annie forced a smile onto her face. "You're going to fight and you're going to win because you're the strongest, most stubborn woman I know!" She nodded firmly to add emphasis to her words.

"And besides..." Annie allowed a real smile to show on her face. "You have to pick yourself up because you've left Vicki alone to manage the lunchtime rush…"

Shirley actually managed a damp chuckle at that. "We can't have that," she said. "Thank you Annie," she gave the younger woman a grateful hug and got up and walked back to her shop.

Annie watched her depart. _You need a better lawyer, and I know where to get one..._

XXXXXX

(Jeff Winger's office)

Jeff had arrived at work that morning somewhat hung over - a not uncommon outcome of nights spent drinking with Britta - and thanked his secretary for the extra strong coffee she made without waiting to be asked. For once, he was grateful to have a full schedule - it stopped him from thinking about what Britta had said.

 _She wants hearts and flowers and romance and all that crap -_ okay, so he didn't stop thinking about it entirely - _probably unicorns and rainbows too. Do I really have time for that nonsense?_ Then he'd remember something - the sight of her peacefully asleep in his car perhaps, or the smile on her face when Troy high-fived him at the end of his trip round the track - and think maybe, _just maybe,_ there could be something there worth a Hallmark card. Then he'd shake his head and refocus on the case Chloe and Michaela were prepping him on before a court appearance the next day.

Thus it was he still hadn't come to a decision when lunchtime came round and he felt his phone vibrate to announce an incoming text message. Seeing the caller ID - "doe eyes, stacked" - he immediately swiped to open it.

 _ **Are you free for lunch tomorrow? Annie**_

 _Well, isn't that interesting?_ Jeff thought to himself with a small smirk. _She's obviously thought about it and decided she doesn't want to miss out._ He typed out a reply which, as well as making it clear he wouldn't come running when she snapped her fingers had the benefit of actually being true.

 _ **Sorry, I'm in court. Wednesday?**_

The reply came less than thirty seconds later -

 _ **Shirley's Snacks, 12:30?**_

Jeff nodded, and sent back a simple thumbs up emoji.

XXXXXX

(Wednesday)

Jeff strode purposefully across the Greendale campus, cashmere overcoat billowing slightly behind him as he conducted an intense conversation on his iphone (he was discussing a new suit with his tailor, but nobody watching needed to know that), finishing as he swept into the Student Lounge and made his way over to the corner set aside for Shirley's Snacks. He smiled softly to himself as he saw a petite figure in a pink cardigan bounce excitedly out of her seat and wave to attract his attention.

Jeff was far too cool to wave back of course, instead he pivoted to change direction and walked briskly over.

"Hi Annie," he said as he leaned forward to kiss her on the cheek. "Good to see you."

"And you Jeff," Annie blushed faintly as she smiled up at him. "Do you want to-" she gestured at a seat. Jeff nodded and sat.

He crossed one leg over another, flicked an imaginary piece of fluff away and grinned suddenly. "Admit it - you asked me here for lunch so the alphas could see you having lunch with the hottest guy to walk these halls since the last time I was here, didn't you?"

"Noooo…." Annie's blush had deepened and she twitched nervously as she brushed her hair over one ear while failing to meet his look. She did however manage to glance sideways to check the cheerleaders two tables away were watching and allowed herself a small glow of satisfaction at the expressions on their faces. She visibly fought to pull herself together. "How much time do you have, Jeff?" she eventually asked.

Jeff shook his head good naturedly. "My name's on the sign above the door, who's going to call me back?"

 _This I can do,_ Annie thought as she sat up straight and beamed at him. "The guy who's name is first on the sign over the door?"

 _Ouch!_ Jeff acknowledged the hit with a good natured wince. He made a production of unbuttoning his cashmere coat, carefully folding it and putting it on an empty chair next to him. Then he linked his hands together in front of him and looked over them directly into Annie's eyes, holding her gaze for a moment until she began to fidget nervously.

"Ms. Edison," he said at last. "In your capacity as student chair of the liaison committee, were you satisfied with the quality of service you received from Petrocelli and Winger in your recent case?"

"Yes, I suppose so-" Annie looked thoroughly confused by Jeff's suddenly businesslike tone.

"And did you feel your concerns were addressed promptly and with courtesy?"

"Well of course-"

Jeff nodded again. "And would you be willing to recommend Petrocelli and Winger to your family and friends?"

"Those who can afford you, yes. In fact-"

"Then Petrocelli and Winger thank you for your kind assistance with this after-case review and we would like to take this opportunity to express the hope you will look to us for all your future legal needs." He suddenly leaned back in his chair, casually rested an arm on his knee, and grinned at Annie. "There - that makes this officially a business lunch, now I can take as much time as I want."

Annie rolled her eyes at him and tutted with amused exasperation.

Jeff sat up suddenly and scrambled for a menu as Shirley approached the table. "I'd like an, aaah-" only to stop as she pulled up an empty chair and sat down. "Can I help you, Mrs. Bennett?"

Shirley looked uncharacteristically uncertain as she looked between the other two. "I was hoping you'd give me some advice on my custody case," she said. "I'm not sure my lawyer's doing everything he can. Annie said it'd be okay," she added, looking at the younger woman for support.

"Did she?" Jeff said, looking at Annie with a face that had gone hard and lost all expression. Annie fidgeted slightly shamefacedly under his stare, not quite meeting his eyes. _Is this why you invited me to lunch Annie, to trick me into giving your friend free legal advice? It wasn't about us at all, was it?_ Jeff was - almost - certain that it was only the reluctance to appear petulant in front of a crowded room that stopped him from picking up his coat and walking out. "Tell me your story, Mrs Bennett." He said instead, shifting his whole attention to the older woman.

"Please, call me Shirley." She said as she nodded gratefully and commenced what was by now a well rehearsed narrative.

 _I'm no expert in divorce or family law but even I can see a couple of things her attorney's missed,_ he thought to himself.

"So, do you think there's anything I can do?" Shirley said as she finished.

"I need to check a few things back at the office, I can probably have something for you in a few days." Jeff sat up in his seat, he noticed in the corner of his eye that Annie seemed to be smiling again.

Shirley got up and took a notebook out of her apron pocket. "I can take your order now, it's on me of course-"

"That won't be necessary, I really do need to get back." Jeff said as he stood and picked up his coat. "It was a pleasure meeting you Shirley, Annie." He nodded cursorily to the young woman, whose jaw had just dropped open with shock, emitting a small squeaking noise. Pausing only to take out his phone, Jeff turned and strode towards the door.

"I'm so sorry Ann-ie," Shirley said slowly as the two women watched his disappearing back with varying degrees of dismay. "This is because you tried to help me." Annie was still speechless as Shirley paused for a moment - she wasn't at all sure she approved of the slick, charming lawyer's interest in her young friend but there was no denying the shocked expression on Annie's face.

"If you really like him and this wasn't just to help me," Shirley said at last. "You can't afford to let him leave here angry."

XXXXXX

Jeff was forcing his anger under control by concentrating on his email messages with all his will. As a result, he didn't hear the flutter of tiny footsteps approach him from behind and overtake him until he almost crashed into something small, pink and angry.

"What the heck, Jeff?" Annie hissed. "Why did you storm out - we were supposed to be having lunch!"

Jeff looked at her for a beat. "Yes Annie, we were!" He said eventually. "So _why-_ " his voice was dripping with sarcastic anger "-did I find myself tricked into giving a free consult to your friend?"

He tried to step past her, she scurried sideways to stay in front of him. "I needed to help Shirley and I couldn't think what else to do, okay?" Annie wailed plaintively.

"You could have asked!" Jeff snapped, temporarily giving up the effort to move past her.

"I wasn't sure you'd do it, at least not for free! And there's no way Shirley could afford to pay you," Annie's tone was now pleading. "I just thought we'd spend a few minutes helping her and then have the lunch we arranged," Annie said plaintively, her eyes huge and damp. "I just didn't think -"

"What, Annie?" Jeff was forcing himself to stay angry in the face of some top-level pleading. "You didn't think I'd be offended at being manipulated? You thought I'd congratulate you on how clever you were?" He took a sudden step to the left, then switched back to the right as Annie followed him, sweeping past her as he caught her off balance and began striding towards the car park at his briskest walking pace.

Annie ran to catch up. "I can make it up to you!" She gasped. "What are you doing Friday night?"

Jeff stopped dead, then turned slowly on the spot until he was facing her, his expression turning from frustrated anger to satisfaction to intense glee.

Annie stood there frozen with shock at what had just come out of her mouth. _Way to make him work for it, Annie!_ A sarcastic voice said at the back of her mind.

"Annie Edison," Jeff said, a triumphant smirk spreading across his face." Did _you_ just ask _me_ on a date?"

"Eeeeee-"

"And it will just be us?" Jeff couldn't resist the temptation to twist the knife while Annie was speechless. "Abed and Troy won't be there asking about intellectual property law for the film, and Britta won't be asking to be bailed out - actually scratch that, Britta doesn't have any problems calling me directly when she needs bailing out…"

"Eeep?" Annie was still so shocked at the turn of events that she could only make random squeaking noises.

Jeff decided to take that as an affirmative. "Nothing I can't reschedule," he said, answering her original question. "I'll let you know the time and place. I'm glad we had this talk, Annie - I'll speak to you again soon." Still grinning, he turned around smartly and began to stride off again, his coat billowing slightly behind him. This time, it looked like a victory walk.

 _So, who ended up manipulating who?_ Annie found herself thinking.

XXXXXX

 _So, with both MR WINGER and MISS EDISON learning to manipulate the other, what will happen next, and will MR WINGER's next effort at a date be more successful than his first? Tune in next time for another episode of "The Road Goes Ever On"..._


	6. Chapter 6

_Previously on "The Road Goes Ever On."_

 _MISS EDISON, feeling sisterly compassion for her friend MRS BENNETT, who's rogue of an ex-husband was denying her access to her children, concocted a plot to trick MR WINGER, an amoral lawyer, into providing counsel. MR WINGER, taking offence at being manipulated, stormed away causing a contrite MISS EDISON to seek to make amends by inviting him on a date. MR WINGER accepted with sufficient alacrity that MISS EDISON was left wondering who, in the end, had manipulated whom. Tune in to this week's episode to see how events unfold..._

 _(Author's note - as a fanfic writer I will always be grateful to the gasleak year for making it canon that Jeff is a tango dancer:-))_

XXXXXX

(Friday morning, early)

"Good match, Cash." Matt Braddock grinned as he firmly gripped Jeff's hand.

"Dammit Turner - I almost had you there," Jeff grinned back as he shook it. It was not a coincidence that he'd arranged a pre-work game of squash with Matt Braddock - Turner - the day of his date with Annie. Braddock, like Jeff and Mark, had worked at Hamish, Hamish & Hamlin. Also like Jeff and Mark, he'd bailed out when he saw the writing on the wall. More relevant to Jeff's purposes, Braddock had headed up H, H & H's family law section and had taken most of their more able lawyers with him when he set up his own practice. It was in his capacity as one of the top family law specialists in the state that Jeff wanted to talk to him.

"Fun though this was," Braddock was still smiling, "I can't believe you called me because you love getting your ass kicked so much."

Jeff nodded, his grin fading. "I need to call in a favour, Matt. A friend of mine," he said as Matt's face went serious, "is going through a messy divorce and custody battle and I think she's being let down by her attorney. Not _that_ sort of friend," Jeff added dryly as he saw the raised eyebrow on the other lawyer's ruggedly handsome face. _Though with any luck_ her _friend might be…_

"Tell me more," the other man said, companionably patting Jeff on the shoulder as they walked off the court.

XXXXXX

(Apartment 303, early evening)

"Yeah, that'll work - guys are suckers for a little black dress!" Britta was helping Annie get ready for her date and Annie had just asked her opinion on the dress she'd picked out - a simple black one, knee length and sleeveless, with a V-neck.

"I've dated before, Britta - I'm twenty-two, not twelve. I have some idea what works." Annie rolled her eyes at her friend's statement of the obvious but smiled gratefully anyway.

"Trust me - with the girls on display like that," Britta pointed at Annie's cleavage, " _nobody_ will be making that mistake."

"Well I'll be wearing this, too," Annie said as she topped it off with a simple green cardigan. "After all it's getting chilly after dark and I'll need to keep my shoulders warm. Do I look okay?"

Britta winced inwardly. She really did want to support Annie, but there was a small selfish part of her that was just - _couldn't you pick somebody other than my friend?_ Angrily, she shook off the jealous moment and forced herself to smile encouragingly. "Yes. You look great. It's a cute sweater and Jeff will really like it," she said, knowing perfectly well as far as Jeff was concerned less is more.

XXXXXX

(Cafe Hermes, 7:57PM)

"Well, he's there." Annie took a deep breath as she pointed to Jeff standing in front of the Cafe, talking into his phone. He obviously hadn't seen the gang in Britta's beat-up old car parked by the side of the road a hundred yards away.

Abed nodded, once. "Operation Annie's Do-Over Date is a go. Do you remember the protocols?"

"You'll text me in an hour before your movie starts to see if I need rescuing and again when it ends," Annie recited. "If I need rescuing and can't speak freely the codephrase is 'is your mother feeling well?' Seriously Abed, I'm sure it'll be fine."

"We can't be too careful." Troy's attempt to sound serious would have worked better if he hadn't been wearing a fedora and trench coat, Sam Spade-style.

"Just remember Annie - you don't have to take any of his nonsense. You're the one in control," Britta added.

Annie beamed. "Thanks Britta. And thanks guys." Annie hugged each of them in turn - somewhat awkwardly in the cramped confines of the car - before slipping out.

The others watched her walk up the road, wave as Jeff spotted her then take his arm when he offered it before leading her inside.

"I can't help think this is a mistake," Britta said with a sigh.

Troy shook his head firmly. "Jeff's a cool guy Britta - he made sure we all had a good time on Saturday, not just Annie. And you should see the way they look at each other when they think nobody's watching - they have real chemistry. I think he can make her happy."

"A woman doesn't need some guy sniffing around her to make her happy," Britta scowled.

"I disagree," Abed said. "Annie needs it. Right now she does. After the year she's had she needs the confidence boost of a good looking high status guy being interested in her."

"I just hope you're right Abed," Britta sighed.

XXXXXX

"Do you know what a _Milonga_ is, Annie?" Jeff asked.

Annie shook her head. She'd deliberately not read up on this venue as, on examining their previous date, she'd come to the conclusion that the amount of research she'd done in advance of it had only stoked her nerves and made it harder to enjoy herself.

Jeff grinned. "Then I'll show you."

Somewhat to Annie's surprise, he led her straight past the bar to the stairs at the far end of the cafe and up them to a large dance floor, where a dozen or so couples were circling to a Latin beat.

"It'll get much busier later," Jeff said, before answering his own question. "A Milonga is a tango party - I've got a table booked for dinner at nine, I thought you might like working up an appetite learning a few practice steps. Then depending on how that went we could come back up for some proper dancing after dinner."

 _That's why you're dressed like a Cuban gigolo!_ Annie thought, allowing herself - another - glance at his sleek black suit, blue shirt and black tie. When first seeing him she'd felt surprisingly dowdy in her simple outfit, but he'd looked at her in a way that made it clear he didn't mind in the slightest.

"That… sounds nice," Annie said, eventually. The smirk on Jeff's face suggested he'd not only noticed the pause but had a fair idea what caused it.

"In that case-" Jeff took hold of her right hand with his left, and placed his right firmly in the small of her back and pulled her to him. Annie squeaked slightly as, not knowing what else to do, she placed her left hand on his right arm.

Jeff adjusted his posture slightly into a more upright position. "The thing to remember about the tango," he said as he used his grip on her to adjust her posture slightly so she was matching his, is that the man is in total control." Annie rolled her eyes as he grinned at her before continuing. "So long as you pay attention to my signals and do _exactly_ what I want, when I want it, then everything should be fine."

"We _are_ just talking about dancing, aren't we Jeff?"

His eyes lit up, but he confined his reply to the subject at hand. "We're going to start off by walking, me forwards, you back-" Jeff led off, Annie following him easily enough. After a couple of minutes he stopped. "You've danced before, haven't you?"

Annie beamed at him. _That surprised you, didn't it?_ "I was a cheerleader in high school and did dance class then to learn how to move, and Greendale offered dance classes to meet the PhysEd requirement so I did a semester of ballroom." She sighed slightly at a memory. "I thought it'd be a fun way to meet guys, but there were only three in our class and they were more interested in each other than the girls," she finished sadly.

Jeff however had only heard one thing. "You were a cheerleader? Do you still have-"

Annie snorted and swatted his chest lightly. "It was my mom's idea, not mine - and I was forty pounds heavier then, with no figure. It really wouldn't do me any favours."

Jeff just looked for a moment as though picturing something. The expression on his face caused her toes to tingle again.

"Shouldn't we be dancing, Jeff?"

He took her back in hold. "As you already know the basics-" and swept off again, moving faster this time.

XXXXXX

Jeff felt somewhat shell-shocked by the time they paused to go down to dinner. This had not been the first time he had taken a date dancing of course, but usually it followed a recognisable pattern - he'd show her a few moves, they'd dance and flirt, he'd show her a few more moves, they'd flirt some more, until eventually he'd hint that if she wanted to see his best moves they'd need to go somewhere more private.

Annie Edison, however, had expected to be taught. And so, after mastering the eight-step basic they'd gone through Progressive Rocks, Cortes, turns, swivels, promenades… with only the bare minimum of flirting.

 _I have a whole new level of respect for the teachers at that place if they had to put up with this for four years_. _On the other hand, if this is how she responds to being taught -_ she was practically glowing with excitement as they headed downstairs.

XXXXXX

Annie had been enjoying herself so much that she had quite forgotten the others were due to contact her, so it was a brief moment of surprise when she felt her phone vibrate before she remembered.

 _ **Are you okay? Do you need rescuing?**_ Abed had written.

 _ **He's teaching me to tango! And no - I'm fine :-)**_

Her phone vibrated again as they reached the table. _**A vertical expression of a horizontal desire - Britta says to be on your guard and remember he's a man.**_ Annie could almost hear her friend's tone of voice - it didn't stop her from blushing suddenly when she looked up and realised Jeff was watching her with a curious expression on her face.

"Anything important?"

"What? No! The guys were just checking to make sure I'm having a good time."

"And are you?" Jeff raised a questioning eyebrow.

Annie smiled softly. "It's going well so far, but I haven't looked at the menu yet."

Jeff winced theatrically to acknowledge the hit, but passed a menu over. Annie relaxed infinitesimally - for a start, she recognised almost everything on it, and ended up ordering a bison burger and a local microbrew to wash it down (Jeff got a sauteed chicken breast with mushrooms, vegetables and quinoa and an imported lager) - and allowed herself a curious scan of the restaurant. It was busy but more relaxed than the French restaurant had been, with as many people in jeans as in suits, and Jeff was almost certainly the sharpest dressed man there - though Annie suspected that would be true in most places, a thought that brought a smile to her face as she looked at him.

"Share the joke?" Jeff asked curiously.

"Oh - just comparing this place to last week's and thinking how different it was."

Jeff grinned ruefully. "Well, showing off what a sophisticated man of the world I am blew chunks," Jeff smirked as Annie gasped in shock at the sudden crudity, "so I thought I'd try relaxing and having fun instead."

Annie suddenly remembered a thought she'd had when he'd helped her out of his car after taking her round the track. "And do all your preferred means of having fun involve socially-acceptable ways of getting close to women, Jeff?"

"I'm sure I have no idea what you mean," he grinned back at her.

XXXXXX

In one respect, this date was like the previous one - they ate in a restaurant and talked. In every other respect it was different: the staff showed no special deference to Jeff's spending power, Annie enjoyed the food she ordered and the conversation was more intimate -

"Do you have any family?" she asked.

"Just my mom. My dad left home when I was eight and I didn't see him again until last year when I tracked him down to tell him I'd made partner despite everything he'd done to me."

"I'm sorry to hear that, Jeff." She looked genuinely sad for him.

He shrugged indifferently. "It needed to be said and I'm glad I said it. What about you?"

"My dad left when was I twelve, my mom disowned me when I was seventeen. I haven't seen her or my brother since."

Jeff's expression was appalled for a moment before shifting to sympathy as he acknowledged another veteran of the Parent Wars. "Jeez, Annie that sucks," he said, raising his glass and clinking it against hers. "Here's to surviving."

And light-hearted -

"So, Troy and Abed - they're gay, right?"

"What? No!" Annie said firmly. "Why would you think that - no scratch that. Just - they're definitely not."

Jeff noticed the way Annie was blushing, but appeared to misinterpret the cause. "Troy brought Britta home, didn't he?"

"They were kinda loud." Annie blushed even more.

And even a little business -

"I talked to an old friend this morning," Jeff said.

"Really, who?" Annie looked curiously.

"Matt Braddock, one of the top family lawyers in the state. He's agreed to consult-" Jeff made an air-quote gesture "-with Mrs Bennett's current lawyer on a pro bono basis."

"Oh Jeff - that's amazing!" Annie was practically glowing with excitement, and Jeff couldn't help but think that the look on her face was worth cashing in a favour.

\- To the extent that when their dishes were cleaned away and they finished the last of their drinks it surprised them both that more than an hour and a half had gone by. Jeff asked her if she wanted to do some more dancing or - but Annie was already out of her seat before he could suggest anything else. They went back upstairs to a hall that was much busier than when they left.

"The party has really started now," Jeff warned. "No more time or space to practice, now we just dance." Jeff's cocky grin was wiped off his face as Annie, who had started to feel warm, took off her cardigan and placed it over the back of a chair. He was quite unable to tear his eyes away as, if in slow motion, she turned to face him and tossed her hair slightly, meeting his eyes squarely with her own. _Wow, just - where the heck did you come from?_ He felt a stir of something approaching awe.

Annie straightened up defiantly, refusing to be intimidated by the suddenly hungry expression on Jeff's face. _Are you ready to see me as something other than one of your usual women yet?_ "Are you ready to dance, Jeff?" she asked softly. "I am."

"Yes, yes you are," Jeff said equally softly. His smile was darker and more intense as he took off his jacket and laid it next to her cardigan before taking her firmly into hold and whisking her out onto the dance floor.

XXXXXX

Annie learned very quickly that a Milonga has certain rules - the DJ would play four tracks at a certain tempo, then pause to announce another set of four in a different tempo. During the pause, those couples who wished would leave the floor or change partners. There was also a rule that dancing and conversation don't mix, so when Jeff proposed getting drinks after the first set Annie happily agreed. She noticed, but did not comment on, the fact that he did not let go of her hand as he led her off the dance floor.

Thus was set the pattern for the evening. They'd dance, then pause to drink, laugh, flirt a little. At one point, Annie found herself remembering Britta's prediction from before the first date - _he'll take you somewhere really nice, spend an evening flattering you shamelessly and generally making you feel like the most important and desirable woman in the world_ \- and found herself rather giddily thinking that, unlike last time, she now knew what Britta meant. (She deliberately tried to avoid thinking about the final part of Britta's prediction - _at the end of it, he'll invite you back to his place and you'll feel really tempted to go_ \- which of course meant she spent some time thinking of nothing else, and wondering what on earth her answer would be if he did ask.)

XXXXXX

"Well that was different," Troy said unenthusiastically as the three friends walked out of the cinema.

Abed was finishing a text message. "We did agree to let Britta pick this time," he said as he put his phone away.

"Yeeeeaaah," said Troy. "I think we should wait a while before we do that again."

Britta looked up. " _Winnie Mandela_ is a movie about a strong independent woman of colour - the fact that you felt so uncomfortable watching it is exactly the reason why you needed to," she said defiantly.

"I didn't like it because it was a terrible movie - and not the good kind of terrible like with decapitations and fake-looking heads going flying everywhere, the bad kind of terrible like with no decapitations at all," Troy retorted. "What do you think Abed?"

Abed considered for a moment. "It was a typical example of the biopic genre, lacking in originality and excessively hagiographic towards its subject. I won't be buying the DVD."

They bickered good-naturedly for a few more minutes as they walked to a bar and Britta ordered drinks. "Have you heard from Annie-" Britta started talking as she joined the boys at the table, stopping suddenly as Abed slipped his phone across. Britta looked at the three most recent messages.

 _ **(Me, 10:58PM) How's your mother?**_

 _ **(Annie, 11:09PM) She's fine Abed, and I'm sure yours is too:-)**_

 _ **(Annie, 11:10PM) You don't have to worry about me, I'll find my own way home. Enjoy the rest of the evening and I'll see you when I get back!**_

"Oh dear," Britta said quietly.

"Maybe I should take tango lessons," Troy said, a slight note of awe in his voice.

XXXXXX

Jeff was exhilarated _._ It was past midnight and the latest set had been faster and more intense than most of the previous ones and the last dance had gone flawlessly. The footwork had been fast and accurate, their bodies had moved in perfect harmony and he'd ended with a dip that left him supporting the whole of Annie's weight in his arms, her body crushed against his, their faces only inches apart and an expression on hers that showed she was feeling it just as much as he was.

"Do you want to blow this joint and go back to my place?" he blurted out as the music ended, unable to hold off for even another second.

Despite the fact she had been expecting this question most of the evening and indeed had pretty much decided what her answer was going to be when she stood Abed down, actually hearing it still took Annie by surprise. Her face must have shown it too, because Jeff started to backtrack as he let her straighten up.

"Erm, what I mean is-" _what the heck's the matter with you, Winger_? Jeff was both dismayed and furious that his instinctive reaction to her surprise had been so uncharacteristic. _She's just another girl!_ But then he allowed himself to look in her eyes. _No. She's not._

Annie felt the moment slipping away. _If Britta's to be believed, then if I do this I'll regret it. But if I don't then I'll regret the might-have-been of it all. If the risk is that I regret it anyway, then I might as well have something to regret!_

"Yes!" she said, taking hold of her courage. "Yes. I would love to go back to your place." She added an encouraging smile. Jeff smiled back with evident relief.

XXXXXX

They wasted no time after that. Jeff pretty much dragged her back to their table to pick up his jacket and her cardigan, then they practically ran outside where he hailed one of the cabs that was arriving to take home drunken partygoers as the evening wound down. The five minute drive to his apartment block felt like forever - for the sake of the driver, they tried to engage in normal conversation, but neither paid much attention to the words they were saying. Jeff never once let go of Annie's hand, gently kneading her palm with his thumb as a statement of intent that had her nerves jangling.

When they arrived, Jeff threw the driver a twenty without even waiting to hear the fare and all but hauled Annie out of the car - she giggled suddenly at the ridiculousness of the situation as he set off dragging her behind him, apparently determined to set a new land speed record for the casual walk. He greeted the doorman with a relaxed "good evening George" - the man didn't blink at the sight of Jeff's companion.

 _Either he's very good at his job or the sight of Jeff bringing a girl back isn't a novel one,_ Annie thought before once again electing not to care. He kissed her for the first time when the elevator doors closed behind them. By the time it reached his floor they were still kissing but Jeff was now carrying her, one arm under her ass and the other across her shoulders. They bumped into the wall twice on the short walk to his apartment - neither of them wanted to stop kissing for long enough to look where they were going - until they crashed into his door. Jeff fumbled for a key and fumbled again for the lock, before finally getting the door open and carrying Annie inside.

Not waiting to turn any lights on, he staggered across a small hallway and through another door, into the master bedroom - somehow managing to kick his shoes off while still carrying and kissing Annie - before finally managing to lower her onto his bed. He still hadn't switched on any lights, but there was more than enough moonlight flooding through the window wall for Jeff to hesitate in the act of taking off his jacket frozen in shock at the sight of Annie reclining on his bed, glowing softly in the silver light. "Have I told you yet just how beautiful you are?"

Annie smiled softly. "It's always nice to hear." She watched transfixed as Jeff took off his jacket and shirt, and the moonlight bathed the hard planes of his body. He grinned back, enjoying the sight of her watching him. As he reached for the belt on his trousers, Annie's nerves, which she had left behind in the nightclub, suddenly caught up with her. "I don't usually do this sort of thing you know," she squeaked slightly, looking away from his eyes.

Jeff stopped what he was doing and sat on the bed next to her, gently taking the tip of her chin in one hand and turning her head so she was looking at him - it was not the first time he'd had to reassure a girl suffering from last second nerves and he had a practiced routine for it. "Then I'm even luckier than I thought I was that you're willing to trust me like this," he said, projecting a sincerity that surprised even him into his voice and his eyes. "If things are moving too fast for you, I have a guest bed-" He stopped talking at that point, shocked at himself - Jeff didn't have (much of) a problem with a girl changing her mind, but he never _ever_ put the idea into her head first. _I guess I really don't want to mess this one up,_ he found himself thinking wonderingly. _And if backing off is what it takes -_

Annie smiled back at him and nodded slightly, as though hearing him take her hesitation seriously had been all she needed to get her courage back. "Just kiss me, Jeff."

Jeff grinned suddenly as the hand that had been holding her chin slipped round to the back of her head and guided her mouth to his, her eyes fluttering shut and her lips parting. She trembled slightly as his other hand found her knee, her back arching into his embrace as it caressed upwards taking the hem of her dress with it.

XXXXXX

Annie drifted into wakefulness the first time when the dawn light was just beginning to show through the windows and the first thing she noticed was the minor aches and twinges of a body that had had an intense workout that had concluded only three or four hours previously. She smiled softly, though there was no one to see it, relaxing into her memories of the night before. _I never thought I'd ever have - It - that good again,_ she thought with a pleased glow.

The glow faded, however, as she realised what needed to come next. She had never been a woman for one night stands, but she had heard enough stories from Britta and read enough articles in magazines that she thought she knew what she needed to do next - slip out without waking him and head out into the morning, head held high. Make him contact her, instead of waiting around to find out what he wanted.

The act of steeling herself to slip out of the bed without waking Jeff served only to make herself aware that she was practically surrounded by him - they were spooning with almost the entirety of the length of her body in contact with his, his head resting gently on hers and and an arm thrown casually across her and the woody musk of his cologne mingling with the scent of her perfume and a light hint of both of their sweat.

As she attempted to wriggle out from under his arm however it suddenly acquired the flexibility and mobility of a steel bar rooted in concrete and pinning her in place.

"Stay Annie, please," Jeff mumbled sleepily as he adjusted his position to pin her body to his.

Annie wriggled slightly, then relaxed into his embrace. "Mmmkay," she mumbled through her own tiredness as she felt her body mould itself to his. _Screw the magazines,_ was her last conscious thought as she drifted back to sleep.

XXXXXX

Jeff woke up next, aroused by the full light of day streaming through the picture windows. He stretched, yawned, allowed himself a moment's happy reflection on the previous night before rolling onto his side and allowing himself to just look at Annie, who had separated from him slightly in the night and now had her back to him. Her silky, dark hair made a delightful mess on his sheets.

Normally at this point Jeff would slip out of bed without waking the girl up, leave a polite note and go off to the gym to give her time to get dressed and leave without him having to talk to her. This time however, and refusing to examine his motives, he leaned over her and planted a soft kiss on her bare shoulder.

Annie rolled over as though the contact had woken her up and as her eyes met his a warm smile spread until it seemed to fill her face. "Hi."

Jeff's hand had reached up to sweep a lock of hair away from her face, she leaned into the contact slightly as his hand brushed her cheek, a small blush flaring. "So - last night," he said softly, returning her smile. "That was pretty amazing."

Annie's smile got even wider, if that was possible.

"In fact-" Jeff grinned as he leaned down to kiss her. Annie's eyes closed and her mouth parted slightly as she stretched up to meet him.

"Do you need to be anywhere this morning?" Jeff finished when they finally parted for breath.

"Oh, I think my schedule's clear." Annie's eyes flicked down to where her hand was drawing patterns on his chest.

"In that case-"

Annie squeaked slightly as Jeff slipped an arm around her waist and suddenly pulled her on top of him.

XXXXXX

They got up, eventually. Jeff showered first, then shaved and dressed in jeans and a t-shirt before telling Annie to make herself at home. She refused to get out of bed until he left the room - Jeff thought her sudden modesty was ridiculous in the circumstances, but left her to it as he went to put some coffee on and start breakfast.

Once she was alone, Annie jumped out of the bed and, without troubling to gather her things, skipped over to the door he had emerged from reasoning (correctly) it must be an en-suite bathroom, albeit on the far side of a dressing room. _Oh we are going to be such friends,_ she thought with a happy smile as she took in his huge - _big enough for two, at least -_ walk-in shower.

XXXXXX

" _Jeff?"_ Annie's voice called from deep inside the apartment

"Out here, babe." Jeff had set up breakfast on his apartment's balcony. A few seconds later, the curtains parted and Annie stepped out. Jeff glanced at her and then did an abrupt double take - she was wearing a bathrobe, her high heels from last night and, as far as he could tell, pretty much nothing else. _Does she have even the faintest idea just how hot she is right now?_

Annie took a seat, adjusted the hem of her robe so it didn't fall open too far, and thanked Jeff when he poured her a mug of coffee. "I put my things in your washing machine and borrowed a robe, I hope you don't mind. Thanks," she said, helping herself to a bowl of the muesli he pushed her way.

Jeff shrugged. "It's for guests."

Annie met his gaze, looked down at the logo on her chest and grinned. "Guests of the Sheraton Las Vegas, to be precise."

"Hey, the rates they charge they expect you to help yourself…"

Annie rolled her eyes at him as she started to eat her breakfast. "The view up here is really nice." Jeff's apartment was sufficiently high up to see above much of the city and clear to the Front Range.

"Yes it is," Jeff hadn't taken his eyes off Annie. She blushed slightly but smiled when she noticed.

XXXXXX

They had a leisurely breakfast, talking about nothing important but enjoying each other's company nevertheless. Afterwards, Jeff gave Annie a short tour of his apartment, starting off with the open plan kitchen/dining/lounge area which seemed to be almost as large as the whole of Apartment 303 -

"If Abed sees that he'll never leave," Annie said as Jeff proudly showed off his 60-inch flatscreen HD TV with surround sound, Blu-Ray player and game console. "Seriously - he'll set up an IV drip of chocolate milk and get Troy to keep him supplied with buttered noodles."

Jeff just smiled, sure that she was joking.

\- And the second bedroom, which Jeff used as a home office. Annie was surprised to see the walls covered with bookshelves, Jeff had not struck her as a particularly literary man -

"Are these Supreme Court judgements?" She asked, pointing at a leather binder that simply said "S.C. 1978-80" on the cover.

"Take a look," Jeff said, suppressing a smirk.

Annie pulled the binder off the shelf and opened it. "' _Spider-Man' comics?_ You - you _nerd!"_ She laughed with surprise. "No wonder you get along so well with Troy and Abed."

Jeff shrugged and grinned, pleased to have surprised Annie. "The law books I own to impress people are kept in my office, the ones I actually use are either online or over there." He gestured towards a pile of much more dog-eared volumes and journals on a desk next to a laptop.

\- And the second bathroom…

"Maybe next time," Annie dismissed with a saucy smile Jeff's suggestion she might want to try the king-size whirlpool tub. Jeff feigned disappointment while inwardly gleefully noting Annie's unforced use of "next time".

They ended up in the utility room, where Jeff kept his sports gear and weights and which Annie had already found. Seeing the dryer had finished, Annie retrieved her things and retreated to the master bedroom - once again, Jeff found himself amused by her modesty as she firmly shut the door in his face. Instead, he contented himself with gathering up the breakfast dishes and loading them in the dishwasher.

XXXXXX

 _Wow!_ Jeff looked up from his tablet to see Annie had emerged wearing her dress from the night before, her cardigan over one arm and her bag on the other. He'd seen her outfit the night before of course, but seeing it in the bright light of day - _just how many different ways is she going to find to shock me with how - wow! - she is?_

She smiled softly as she saw his expression. _I could get used to you looking at me like that_. Then she frowned slightly as she looked down at her outfit. "I've never done the Walk of Shame before." She couldn't quite decide whether she was ashamed of that or pleased to have ticked yet another milestone off on her long journey to adulthood.

"And you won't today," Jeff said firmly as he got up. "Of course I'm going to take you home - just give me two minutes to get a jacket."

Annie beamed gratefully at him as he slipped past her and disappeared into the bedroom.

XXXXXX

(Apartment 303)

"They're back," Abed said. Troy and Britta scrambled over to join him at the window. For the past half hour, since receiving a text from Annie saying Jeff was driving her back, they'd been taking it in turns to watch out for them.

"Do you think they did it?" Troy said, watching as Jeff helped Annie out of the car.

"Oh, they did it all right," Britta said with a faintly disapproving tone to her voice. She watched as Jeff leaned forward to kiss Annie goodbye, only for the kiss to get deeper and more intense until Jeff was standing upright and both Annie's feet were off the ground and curled up behind her.

Troy looked at Abed. "Pancakes?"

"Pancakes," Abed confirmed. The guys did their special handshake to celebrate.

"What do pancakes have to do with anything?" Britta asked as she turned away from the spectacle down below.

XXXXXX

 _So with MR WINGER and MISS EDISON having taken their relationship to a new level, what will happen next and how will their friends react to this? Tune in at the same time next week for another episode of "The Road Goes Ever On"..._


	7. Chapter 7

_Previously on "The Road Goes Ever On."_

 _MR WINGER and MISS EDISON had a second, much more successful, date in which their relationship reached new levels of understanding and intimacy. But what of MISS EDISON's friends? Will they be as accepting of the place the slick lawyer has taken in her life? Tune in to this week's episode to see how events unfold..._

XXXXXX

September 16th - Morning, Offices of Ditcher, Hyde & Runne (" _Divorce is for life, not just for Christmas!")_

Shirley knocked on her lawyer's office door with some trepidation. She'd received a message late on Friday asking her if she could come in today - Monday - and, after confirming that Vicki was free to open the shop, had agreed.

"Hello?" Shirley opened the door, puzzled to see her lawyer, Ralph Ditcher, was not on his own.

"Ah, Mrs Bennett-" he said, looking rather queasy. "Allow me to introduce Matthew Braddock, from Braddock, Finch & Dale. I invited-" he hesitated slightly on that word "-him to consult on your case and he's graciously agreed."

Shirley turned to the other man in the room, a distinguished looking African-American gentleman a few years older than her and wearing an expensive suit that fit him just right. He smiled warmly at her as he reached to shake her hand.

"Please to meet you, Mrs Bennett," he said. For some reason, Shirley found herself thinking of Morgan Freeman as she listened to his rich, mellow voice.

"Pleased to meet you too," Shirley said as she shook his hand. "But I don't think I can afford-"

"Mr Braddock has agreed to consult pro bono," Ditcher said in the background.

"I understand things have not gone well for you Mrs Bennett," Braddock said. "I'm here to change that - tell me everything," he finished firmly.

"Well you see Mr Braddock-"

"Please, call me Matt."

Shirley suddenly felt herself smile wholeheartedly for the first time in a long time as a great weight shifted. "Well you see Matt-"

XXXXXX

"Are you feeling well Jeff?" Mark said, an amused grin on his face - the two men were having their weekly lunch on Monday as Mark was travelling down to Pueblo to represent a client in court. He expected to be there for the rest of the week and was effectively leaving Jeff in charge of the office.

 _No,_ Jeff thought. Oh, he had a routine for when he slept with a girl he liked enough to want to see again - he'd wait at least a couple of days before getting in touch to let her build up a head of steam, and wait a couple of more days after that before asking her out again. He'd fully intended to do the same with Annie after dropping her off on Saturday.

Instead, his resolve had barely lasted until evening on the same day when, settling down in front of Netflix with a low carb beer he'd taken out his phone and texted her. And worse - the next day he'd jumped into his car and driven an hour to his mother's house for Sunday dinner to avoid turning into a complete teenage girl by driving down to Annie's place and begging her to spend the day with him. He'd actually been relieved to come into work today.

He raised an eyebrow at Mark. "I'm fine, why?"

His friend was still grinning. "Only that that waitress has been flirting with you non-stop since we arrived and you've barely acknowledged her."

"What waitress?" Jeff still sounded puzzled.

"The blonde with the legs-" Mark pointed to the other side of the restaurant. Jeff turned and smiled back warily when she smiled at him before turning back to her customer.

"Maybe I'm just not interested," Jeff said.

"She's hot and has a pulse." Mark said it as though it refuted Jeff's comment.

 _If you spend your time eyeing up other women she's not going to be happy_ , Britta's voice said in the back of his head. He dismissed it with an invisible shudder and looked across the table square into Mark's eye and put on his best 'aren't-I-sincere' voice. "Maybe I'm maturing, learning to value women as people and not just as sex objects."

Mark had known Jeff for far too long to be taken in. "Who is she, Jeff?" he said with a wry smirk. "You haven't been this off your game since you were seeing the professor."

Jeff grimaced slightly at being reminded of Michelle Slater. "I've no idea what you mean," he mumbled.

"Heck, even the hippy didn't move you past 'look but don't touch'..." Mark twisted the knife before pausing for a moment to enjoy Jeff's discomfiture, then his face lit up as though remembering something. "It's the college girl, isn't it? The one you came up with some lame excuse to bring back to the office?"

 _Sheesh - this place is crawling with gossip!_ Jeff hadn't even been aware that Mark had known about Annie's visit to the office. "Weren't we talking about the United Holdings case?" he mumbled instead.

Mercifully, Mark decided to go easy on Jeff and allow him to steer the conversation back to the cases that Jeff would be covering in his absence. Jeff was less successful at distracting himself than he would have liked however, and as they walked back to the office he'd fished out his phone and, cursing his weakness slightly, fired off a simple text message.

 _ **Dinner tonight?**_

His phone vibrated to announce a reply just after he got back to his desk.

 _ **So long as it's just dinner! I have a test I need to study for:-(**_

 _We'll see about that,_ Jeff smirked to himself as he fired back a thumbs up.

XXXXXX

"B+ Miss Edison, not your best work." The teacher said as he handed back the marked test paper.

"Sorry Dr Isakson," Annie said insincerely, surprising herself as she did so. Annie knew perfectly well why she'd practically failed the test - she'd gone to dinner with Jeff the night before promising herself that it was only dinner and she'd spend the rest of the night studying. That promise had - more or less - held up until the moment that he'd taken her back to Apartment 303 only for a goodnight kiss before she got out of the car to turn into something more intense and then into, well, Annie ticking off another milestone on her road to being a well-rounded adult.

After she'd finally - _finally -_ managed to disentangle herself and arrange her clothes into some sort of order she'd marched back indoors glaring at Troy and Abed, defying them to say anything. Then, instead of studying straight away, she'd spent the first half of the evening going through her big wedding binder wondering what arrangements would need to be adjusted to cope with a much larger than expected height difference between the bride and groom. _Maybe we could have the official pictures taken on a grand staircase somewhere,_ she thought. _Or we could have him sweeping me off my feet…_

"I'll do better next time-" she stopped talking suddenly when she realised that the teacher had already moved on to the next student.

 _At least I know I won't have to worry about picking out a suit…_

XXXXXX

 _ **What are you doing tonight?**_ It was Wednesday and Annie was texting Jeff.

 _ **Burning the midnight oil:-( I'm in court tomorrow and if I'm not thoroughly prepped the DA will own my ass.**_ It was 9:30, but Jeff thought the metaphor would hold.

 _ **It's 9:30, not midnight!**_ Jeff smiled softly at that while allowing himself a mild eyebrow raise of surprise at Annie apparently being able to read his mind despite not even being in the same room.

 _ **Your pedantry is one of the hottest things about you**_ \- Jeff started to reply.

"Mr Winger? The pizza's here." Michaela said. Jeff jumped slightly in surprise - at some point in the evening she'd kicked her shoes off and as a result he hadn't heard her approach. _Not even Wonder Woman can be expected to spend over ten hours in four inch heels_ , he thought wryly.

\- _**sorry babe, duty calls:-( Speak to you tomorrow…**_ he finished his text to Annie before turning to the associate who was helping him prepare.

"What have I told you, Michaela? It's after hours, you're allowed to call me Jeff." He grinned wryly at her as he reached for the pizza box.

"Whatever you say Mr Winger," she replied with a small smile of her own. It wasn't the first time they'd had this exchange - Mark was of the opinion that one of the reasons Hamish, Hamish and Hamlin had collapsed was a corporate culture that encouraged frivolity, familiarity and indiscipline and he'd insisted on certain ground rules of behaviour during office hours. Jeff was of the opinion that office hours meant exactly that and it should be possible to relax outside them, but Michaela seemed to take the view that if she maintained the rules at all times she wouldn't forget when it was important.

 _You're probably right,_ Jeff admitted to himself as he watched her set out the cups of Diet Coke that had also been delivered. He idly noticed that her auburn hair was somewhat fetchingly disorganised and the hem of her blouse was no longer tidily tucked into the waistband of her skirt which - along with the shoelessness he'd already registered - went to show the long hours were affecting her too.

 _If I wasn't seeing Annie it would be very easy to -_ but he shook his head. _No, I'd still be your boss. Mark was right about that - I hate it when other people are right!_ He grinned suddenly.

"Something funny, Mr Winger?"

Jeff pointed at the pizza. "Half Vegetarian Heaven and Half Meat Feast," he said. The people at the pizza place must think I'm schizophrenic," he said as he grabbed a meaty slice.

XXXXXX

 _Abed's having a movie night on Friday and you're invited!" she'd said. "We'll be watching all the Police Academy movies!"_

" _HaHaHaNo," he'd said._

" _Pleeeeeeaaaaasse! Do you have any idea how many there are and how terrible they get? I can't sit through them all on my own!" she'd said._

" _If you need my company that desperately you can always come over-" he'd said._

" _I can't! I promised the boys I wouldn't bail on them this week!" She'd said._

 _Sorry babe, I'll make it up to you on Sat-" he'd said._

" _You can bring an overnight bag!" she'd practically yelled into the phone._

" _..."_

Jeff smiled ruefully at the memory of the bizarre process that had led him into taking an Uber to Apartment 303 and standing outside the door with a case of beer (decent stuff, not the sort students could afford) under one arm and an overnight bag over his shoulder. He adjusted the balance of his load slightly and knocked on the door.

"Glad you could make it Jeff," Troy beamed at him as he opened the door. "Let me take that off you-" Jeff passed the beer to him.

"Brains?" Troy said, looking faintly puzzled.

"It's imported," Jeff said as though that was an answer. Then he grinned. "And besides, I thought it was something you college types could use more of."

"Yeah," Troy said, smiling wider as he felt the weight of the case.

"Now if you'll excuse me buddy-" Jeff turned away from Troy to the petite brunette practically vibrating with eagerness behind him.

"Hi babe," he said, sweeping Annie into an enthusiastic embrace.

"Glad you made it Jeff," Annie's return embrace was equally enthusiastic.

"I just want to say one thing," Jeff said, an expression of mock seriousness on his face. "I don't want you to think you can get me to do whatever you want by promising me sex. I mean you _can_ , but I don't want you thinking that way."

" _JEFF!"_ Annie gasped in shock as she swatted him lightly across the chest. However her expression soon turned into a pleased smirk as her eyes lit up and met his.

" _We haven't eaten yet, you two!"_

"Good to see you too Britta," Jeff said dryly as he turned to face the rest of the room.

"Hi Jeff," Abed said.

"So it's true!" boomed an English accented voice, the owner of which was somewhat unsteadily rising to his feet. "You were barely on site for five minutes and still managed to bag the ripest filly on campus!"

Annie squeaked in outrage where she was standing next to Jeff.

"Duncan, you're drunk." Jeff said blandly.

"Hardly, dear boy." The other man replied amiably. "I'm barely even tipsy - as the evening progresses I do however fully intend to get wrecked, before moving on to be bladdered, then slaughtered before ending the evening thoroughly ratarsed - oh, thank you my dear." He said as Shirley handed him something. He sniffed disdainfully at it, before drinking it anyway. "Fruit juice," he mumbled.

"What _are_ you doing here?" Jeff asked.

"We invited the whole committee over," Annie said. "More team building was needed, the dean said." She added apologetically.

"Does that mean-" Jeff was interrupted before he could complete his sentence.

"Oh - is that Mr Winger?" said a familiar bald headed man as he appeared from out of the bathroom.

Jeff pulled Annie even tighter into him. "You're staying next to me all evening," he muttered.

XXXXXX

Jeff meant what he'd said. When Abed called everyone to take their places and watch the first film he made sure to grab the small couch first and spread out enough so that there was only enough space for Annie to fit on beside him (diligently ignoring a rather unsubtle attempt by the dean to squeeze in between them). They'd started out side by side, but by the end she was curled up against his side and his arm was draped over her shoulder.

"Excuse me babe - I've got to get another drink," he whispered as he sat up. He picked up his glass, looked at Annie who nodded gratefully back at him and picked up hers as well.

By the time he'd got to the kitchen counter, Britta had also got up and walked over to join him.

"So, you guys were looking pretty comfortable over there." She said, her expression unreadable.

Jeff looked over to where the petite brunette was sitting. "Yeah, Annie's pretty special."

Britta saw the expression on his face and sighed slightly. "Just remember this, Jeff-"

Jeff turned back to face her, a curious expression on his face.

"-The people in this room barely know you, but they all know Annie. And care about her. A lot. If you hurt her in any way -" Britta stopped talking and simply drew a thumb across her throat.

Jeff frankly doubted he was in much danger from anyone in the room, but nodded seriously anyway before breaking into a huge grin.

"So if you and Annie are such good friends, then maybe-"

"Finish that sentence and die, Winger."

If anything, Jeff's grin got even wider.

"-you know what her birthday is?" he finished. "I don't want to miss it." He picked up the glasses he'd refilled and ironically saluted a now speechless Britta with his before swaggering back to Annie, who by now was trying hard not to fret about what had been keeping the two of them.

"What did Britta want to talk about?" She said.

"Oh, she was just threatening me."

"What for?" Annie shifted to glare at Britta.

"She wanted to make sure I understood what a horrible fate lay in store for me if I ever hurt you."

"Aww," Annie's glare turned into a glow of happiness as she snuggled back into his side.

Jeff wrote that incident off as Britta being Britta, and when Shirley came over to talk to him the next time he went up for drinks - ostensibly to thank him for the introduction to Matt Braddock, only to segue smoothly into a deeply disturbing anecdote about a stripper and a jukebox - he assumed it was a coincidence.

He spotted a pattern when the third time he went up Troy joined him.

"You're a cool guy Jeff, but Annie's awesome and any guy who upsets her-"

"Troy, are you doing a Forest Whitaker impersonation?"

Troy's threatening expression immediately shifted to a big grin. "Dude! You got it-" then he remembered what he was supposed to be doing and put his serious face back on.

"It's okay Troy, I get the message."

And he was wearily resigned to it when the fourth time Abed came up, only to be pleasantly surprised when he started talking about something completely different.

"Have you ever seen _Taken_ Jeff?"

Jeff nodded agreeably. "It's one of my favorite films, Liam Neeson is outstanding in it."

"You're wrong," Abed said flatly. "It's an inferior rip-off of the _Death Wish_ franchise and Neeson barely qualifies as a second rate Charles Bronson. He did have the right idea about how to treat men who hurt women he cares about however."

 _Oh,_ Jeff thought. "Message received Abed," he sighed.

"Cheers Jeff."

By the time Jeff went up for the fifth time, he had a certain morbid curiosity as to who would approach him this time. With only two left he wasn't surprised to see Ian Duncan stagger over.

"Out with it, Duncan." Jeff grated out.

"What?" for a moment Duncan looked too distracted by the search for a bottle that still had some liquor in it to understand what Jeff was referring to. "Oh yes," he finally remembered. "Big boobs. Lovely girl, very bouncy. Try not to be too, well, you."

Duncan pivoted until he was more or less facing Jeff and poked him haphazardly in the chest. "I have a cousin in the SAS, you know." He said in a fake whisper.

"Do you? Really?" Jeff was honestly astonished.

"Whaaa-" Duncan regathered control of himself. "Not the faintest idea. Secretive buggers, the SAS. Better safe than sorry, eh?" He jabbed Jeff one last time then pivoted away from him and staggered slowly back to his floor cushion next to Britta.

The next time Jeff needed a drink he sent Annie up. He really had no intention of finding out what threats the dean had in mind.

XXXXXX

"I'm tired," Annie yawned. They were about halfway through the fourth movie and midnight was a distant memory as the now distinctly tipsy audience was gleefully yelling abuse at the TV screen.

"Oh, sorry-" Jeff leapt upright. "Do you need a pillow?"

"No I'm too tired for that," Annie looked Jeff straight in the eyes. "I think I'll go to bed."

" _Bed,_ Jeff…" she hissed when he failed to respond.

"Wha - _ohh..._ " an understanding grin slowly spread across his face as Annie got up and padded over to the bathroom. Shortly afterwards, she fixed him with a meaningful stare as she headed back again and slipped into her bedroom.

Jeff faked a huge yawn, grabbed his overnight bag and followed her. "You know, I think I'll just crash out on the floor…"

Everybody was ostentatiously watching the TV by the time he slipped into Annie's room.

Abed didn't say anything, instead he just reached for the remote and turned the sound up a few notches.

"Did you really need to do that?" Shirley asked.

"Oh yes," Troy and Britta said simultaneously, somewhat to each other's surprise.

"I don't want to know how you two both know that." Shirley grumbled.

"It's because they've both-" Duncan started.

" _I said_ I didn't want to know," Shirley growled dangerously.

XXXXXX

It really wasn't Jeff's fault.

As a single man who lived alone he rarely bothered to get dressed in order to make the short journey from his bed to the bathroom. When he awoke in the morning he lay still for a moment enjoying the softness and warmth of Annie's body against his and the smell of her hair in his nose before another, more, urgent need claimed his attention.

Still more than half asleep, he clambered out of the bed, staggered over to the door and stepped through it only for a sudden high-pitched squeak to jerk him fully awake.

His eyes snapped into focus, only to see Shirley - who had clearly got up early to prepare breakfast - staring at him, frozen in shock. Jeff flashed her a weak smile before diving back into the bedroom, emerging shortly afterwards with a towel around his waist.

"Good morning Mrs Bennett," he said as though it was the most natural thing in the world.

"Boy, after what I just saw you really need to start calling me Shirley." She said in her best judgey voice.

"Yes Shirley," Jeff mumbled as he scurried to the bathroom.

By the time he'd showered, shaved and combed the barest minimum of product through his hair and emerged again everybody else had risen - Britta practically elbowed him aside in her rush to get into the bathroom next.

"Good morning everyone," Jeff said to the assembled multitude gathered around the kitchen counter, acknowledging their responses on the way back to Annie's room and pretending not to notice the dean, whose eyes had gone as wide as dish plates before he hastily scrambled to grab his phone.

"You know I don't approve of pre-marital shenanigans," Shirley said to Annie as the bedroom door closed. "But if you're going to sin there's an argument in favour of doing it properly," she added gruffly. "That's one fine looking boy."

"Thanks Shirley," Annie beamed happily back at her.

Jeff re-emerged ten minutes later, wearing jeans and a lumberjack shirt which he had chosen the day before to portray just the right blend of effortlessly casual yet rugged masculinity.

"Good morning babe," he said as he kissed a beaming Annie - on the cheek - before sliding on to the empty stool next to her, for all the world as though he hadn't spent the night in her room.

Thanks Shirley," he added as she silently slid a plate of bacon and eggs over to him.

"So, what's everybody doing today?" he grinned at the silent group.

XXXXXX

 _So, with MISS EDISON's Greendale family willing to give MR WINGER the benefit of the doubt, are there any obstacles left in the way of our leading couple living happily ever after? Tune in next time to the final episode of "The Road Goes Ever On"!_


	8. Chapter 8

_Previously on "The Road Goes Ever on."_

MISS EDISON, an innocent bluestocking, invited her new paramour MR WINGER, an amoral lawyer, to meet her friends. After an evening taking his measure and warning him about how they expect him to behave towards her they have begrudgingly accepted him into the bosom of their small Community. MISS EDISON however has started to worry that MR WINGER has yet to reciprocate this gesture and is beginning to feel concerned that he does not hold her in the same high regard she does him. How will she address this situation? Tune into the final episode to find out!

XXXXXX

(Apartment 303, Saturday morning)

"Your room is very… you," Jeff said dryly. He was sitting on the edge of Annie's bed pulling his jeans on.

"I have no idea what you mean," Annie said, equally dryly. She was sitting up in bed, the sheet pulled modestly up into her armpits and smiling a little as she watched him.

"The cute furniture, the stuffed animals - which I am trying really hard to believe are a nostalgic connection to childhood-" Jeff said.

Annie smiled nervously and broke eye contact.

"-and the overloaded bookcase. Which is only to be expected from the hottest nerd in the state." He grinned and winked at her, she blushed but smiled back.

Jeff turned back and looked closer at the bookcase, his curiosity aroused. He dismissed the top half with a simple "college text books? Boooring…" which earned him an eye roll from Annie.

Then -"Jane Austen? And _Twilight?_ Oh Annie…" he shook his head in mock disapproval.

She pushed him with her foot through the blanket. "I can't help it - I'm the target demographic," she mumbled.

"Wait a minute, what's this?" Jeff's eye had been caught by a large, furry binder on the bottom shelf. That's not a book-"

Annie saw what he was pointing at and shot upright. "No Jeff, that's… personal!"

He paused in the act of leaning over to fetch the binder and instead turned to focus his attention on Annie, a mischievous smirk spreading across his face.

"Too personal to share with me?" he said waving at the bed, his meaning obvious. "What is it - love letters from old boyfriends?"

"What? No!"

Jeff's smirk got even wider as he saw the flustered expression on Annie's face. "Oh, I know - you paid your way through college doing some adult modelling and that's your portfolio…"

"No! And eeeww!"

"Pity." Jeff's grin had acquired a more lascivious touch which caused Annie to blush slightly amidst her consternation.

"Seriously babe," Jeff adjusted his expression to match his words. "What can be so bad that you're afraid even to tell me what's in it?"

"It's not bad, it's just embarrassing." Annie mumbled.

Jeff didn't say anything, he just looked at her as though expecting her to continue.

She sighed. "Ever since I was a little girl I've loved weddings and everything about them."

"Really, Annie?" Jeff frowned. "Marriage is a lie, promoted by-"

"I didn't say marriage Jeff - I said weddings." Annie interrupted sharply. "I've told you the sort of childhood I had, can you blame me for dreaming about something bright and fun and optimistic? There was nothing like that in my life." She threw herself back on her pillow with an exasperated sigh. "So, fine - take a look if you want to. See what sort of silly little girl you've saddled yourself with."

"Annie, it's okay-"

"No Jeff, it's fine - I don't want you wondering what's in there."

Jeff hesitated for another moment, but his curiosity was by now intense. He reached over, pulled out the binder and started flicking through. There were blank wedding invitations, photographs of bridal bouquets, fabric samples, pictures and designs of wedding dresses (all focussed on the petite figure) and shoes. Jeff started noting a theme appearing as the most recent samples in the last category were much higher heeled than the earlier ones - _as though she's thinking about how to minimise a height difference -_ a suspicion which seemed to be confirmed when he got to the section on wedding pictures and saw a shift from relatively conventional ones where the couple were standing side by side to ones where they were standing on a grand staircase, or the groom was carrying the bride or she was leaning out of a window or over a balcony as he stretched up to kiss her, again as though trying to disguise a large height difference.

"Annie, do I have to worry about this?" he said quietly, as though fighting down an urge to panic. "Are you planning our wedding?" _We've been together less than a month!_

"No, I was just daydreaming. You can't have a wedding without a groom. You're lucky - I've only married you once. I've married Troy-"

" _What?"_

"He was the best looking guy in high school," she said hurriedly. "And I've married Rich and Vaughn. And Clint Hightower at least half a dozen times, " she said bitterly, causing Jeff to recall Britta's tale of catfishing.

"And Zac Efron. Mostly Zac Efron, sometimes Mark Ruffalo," She finished with a small smile. "Obviously I haven't actually married any of them, or even really wanted to. I just like weddings and I like planning things."

"Does Zac get any say in this?" Jeff still looked a little sceptical.

"I don't know," Annie was getting a little tired of being defensive. "I mean, it's not as if you're perfect either - it hurts a little that you haven't introduced me to your friends yet-"

"My friends are very busy people," Jeff mumbled. _And not really friends like Troy and Abed are for you..._

Annie overrode him. "And you don't even call me your girlfriend when we're out! Can you blame me for wanting to imagine there's something real between us?" She'd sat up again, still clutching the sheet, and was glaring at him by now.

"The last time I called someone a girlfriend it didn't end well." Now it was Jeff's turn to sound bitter.

"Britta?" Annie looked confused. "But you guys are fine-" _a bit too fine if you ask me._

"Britta's a friend who's a girl, not a girlfriend. She was back then too, and both of us were fine with it. That's not who I was talking about. It was actually the very first time I got involved with Greendale -" Jeff was avoiding meeting Annie's eyes, his face set and grim as he briefly ran through the details of his time with Michelle Slater.

"Oh," Annie was speechless with disbelief. _You dated Professor Slater? Just how many times did our paths almost cross?_

"Yeah," Jeff said. Then, with a conscious effort of will, he moved the conversation on to a lighter topic. "Well, I can tell you one thing your fantasy got wrong." He said wryly. " _If_ we were getting married, I wouldn't be posing for cheesy pictures on staircases. And balconies are right out," he suddenly grinned at her. "And a _rented_ tuxedo?" he pointed at a flyer with a visible shudder. "No girl is worth that."

Annie smiled back. "I thought you could be trusted to buy your own suit."

XXXXXX

The rest of the morning passed quietly. Annie kicked Jeff out of her room - as always, her sudden modesty amusing him - so she could prepare for a shower and get dressed. He stayed for breakfast, afterwards saying his goodbyes with a hug (for Annie) and handshakes for Troy and Abed - they'd invited him to come with them to Colorado Springs to see where Stargate had been set, but he declined citing cases to review.

XXXXXX

Things subtly changed after that. The wedding binder disappeared into a storage box at the back of Annie's wardrobe and she started wearing suits and trousers more (she drew the line at packing away her favorite stuffed animals). She also vowed to be less 'clingy' in dealing with him, but it did rankle her somewhat that some subjects were now off-limits.

XXXXXX

"I mean, I'm not sure I know where I stand with him," Annie said sadly. It was a week later and she'd met up with Britta and Shirley for another Girl's Night.

"He's never called me his girlfriend or introduced me to his friends, and when I challenged him on it on it he said it was because he got burned by his last real girlfriend, but why should he hold that against me? I mean we go out, we have fun we… spend the night together," Annie's voice dropped to a bare whisper as she quickly checked nobody was overhearing them.

"Oh we know what you do," Shirley said severely. "But that's not being in a relationship. If that's what you want you shouldn't have given him what he wanted so soon - after all, why would the farmer buy the cow when he's getting the milk for free?"

"Shirley!" Annie squeaked. Then -

"Britta!" Now thoroughly flustered, she turned to her other friend. "Help me out here!" She hissed.

Britta, who had been trying to turn invisible while the argument wore on, was somewhat taken by surprise to suddenly be drawn into it, but rallied quickly. "We live in a patriarchal, sex-obsessed society where men are constantly trying to take control over our bodies away from us, Annie! Let them do it and you'll never get it back. Look - Jeff's a good guy to have fun with, but he has the emotional depth of a fortune cookie saying. If you want something serious from him you need to make him work for it."

"You gave in too soon," Shirley repeated her point. "Now he holds all the cards."

Annie was feeling cornered and stressed. " _I_ gave in too soon? What about Britta - she slept with him before she even found out his name!" She glared defiantly at her blonde friend, who looked like her breath had been knocked out of her.

"He told you that?" Britta finally managed to gasp out.

"No, you did!" Annie hissed back. "When you were really drunk one time!"

"Oh," Britta slumped back into her seat shamefacedly.

Shirley glared at Britta - this was news to her. "Let this be a lesson to you Annie," she said. "Give yourself away too easily and you'll end up like Britta - alone in your thirties and sleeping with anybody who asks."

"Shirley!" Annie was shocked.

Britta was furious. "Or you could throw yourself at the first guy who smiles at you and end up like Shirley - alone in your forties and sleeping with no-one!" She hissed back.

"Britta!" Annie gasped.

The three women sat in frosty silence for a moment, glaring at each other. Annie broke it first.

"We're supposed to be friends," she sighed.

"Sorry Shirley," Britta mumbled. "You've been a good mom to all of us as well as your kids, even if it does mean consenting to a role Society wants to force all women into."

"Thank you, Brit-ta-" Shirley paused in her response as Annie glared at her. "And I'm sure I'm sorry too," she added grudgingly. "Your heart's always in the right place, even if we can't say the same about your body."

Britta decided to let that slide the same way Shirley had. "Let's never let Jeff divide us again," she said instead, brightening up slightly as she raised a glass in a toast.

"Uh-hmm," Shirley nodded, raising her own glass.

Annie suddenly sat up in her seat with an excited grin on her face. "You guys won't believe who the ex who managed to hurt him was -"

XXXXXX

Annie spent most of a day thinking over what her friends had said. By late afternoon, she had reached a decision - very early on in their relationship she had taken a conscious decision not to allow his previous relationships to affect them. Surely it was only fair to expect the same from him? No. It was time for Annie Edison to take control and demand the answers she was entitled to, and if he was unwilling or unable to provide them, There Would Be Consequences.

Thus resolved, before she packed away her work she sent him a deceptively simple email.

 _ **Are you free tonight?**_

It took just over a minute for a reply to arrive.

 _ **Sorry babe, but something's come up at work. I'm going to be late - I'll let you know as soon as I'm free. Hope to see you soon.**_

Annie silently screamed with frustration. _Dammit, Jeff! You had better not be playing me!_

XXXXXX

(Offices of Petrocelli and Winger)

"To Chloe and Michaela, the newest licensed attorneys at Petrocelli and Winger!" Mark announced to applause from the rest of the office as, to further applause, he popped the cork on a magnum of champagne.

"Well done ladies," Jeff said as he raised a glass in salute. "You realise it only gets harder from here, don't you?" he added with a grin.

"Don't listen to him," Mark said, beaming like a proud father. "Passing the bar exam is a huge deal, and tonight the partners will be taking their newest lawyers out to dinner to celebrate. I trust you're both free for the evening?"

Chloe and Michaela looked at each briefly, then nodded. "Yes, Mr Petrocelli." Chloe said.

"Call me Mark," he said, still beaming indulgently.

Jeff excused himself after a few minutes when he felt his phone vibrate. It was an email from Annie.

 _ **Are you free tonight?**_

Jeff's smile slipped slightly as he composed a reply, even if Annie had been a bit… strange recently he didn't like to turn her down.

 _ **Sorry babe, but something's come up at work. I'm going to be late - I'll let you know as soon as I'm free. Hope to see you soon.**_

XXXXXX

Craig Pelton would be deeply offended if you described his behaviour as stalking. Yes, after reading Annie's latest exchange with Jeff he'd decided to drive down to the law firm in the hope of spying out what the lawyer was up to instead of seeing her, but...

No - as dean, he had a duty of pastoral care to monitor his students' email messages. And it was especially important that he do so when those students occupied important positions in the school government, such as the members of the liaison committee. And when one of those students entered into a grossly unethical and immoral relationship with the school's attorney (okay, he wasn't on retainer - but he'd taken on one case already, and could easily take on others in the future so it counted, right?) well, he would be failing in his duty _not_ to monitor the shameless hussy's correspondence, wouldn't he?

No, the dean knew this relationship was not in Greendale's best interests. Yes, it was in the school's interests that the lawyer be kept close, but it should be by someone older, worldlier, someone who could handle him, control him, (he shuddered deliciously at this point), not a silly little girl! Not even one as terrifying as Annie Edison. No - _ooh! That's interesting!_ His reverie had been interrupted by the sight of Jeff Winger's Ferrari pulling up to the security barrier of his firm's parking lot, but what had really interested him was that he was not alone, for in the passenger seat was an attractive young woman. As the Ferrari cleared the security barrier, Pelton started his own vehicle and slipped discreetly into the other car's slipstream.

 _XXXXXX_

 _Le Relais des Arts_ restaurant

"Have you eaten here before, Jeff?" Michaela asked as they walked up to the restaurant from the parking lot. At the office, Mark had explained that full lawyers were on first name terms.

"Not for a month," Jeff suppressed a small shudder at the memory of his previous visit. _Even if it did work out okay in the end_ \- "Mark made the booking, it's a particular favorite of his. After you -" Jeff held the door open, genially ushering her in ahead of him.

Michaela smiled her thanks at him before waving to somebody at the bar. "Oh look! Mark and Chloe are already here-"

Neither of them noticed the small car parked on the other side of the road with a bald headed man leaning out of it, frantically taking pictures with his phone camera.

 _Let's see if she still trusts him when I tweet this!_ Craig Pelton thought exultantly.

XXXXXX

Apartment 303

"Hi guys!" Annie said brightly. When Jeff had said he was too tied up with work to meet up she stayed behind to catch up on some committee paperwork and as a result had got home over two hours later than Troy and Abed. "I bought take out - what is it?" She'd noticed the sombre expressions on the boys' faces.

Troy looked at Abed, who nodded once. "You have to see this Annie," he said, holding out his phone.

Annie looked at the screen. It was displaying the dean's twitter feed, and on it was a picture of Jeff walking into a restaurant with an attractive, stylishly dressed auburn haired young woman who was smiling at him as she walked in ahead of him, his hand hovering over the small of her back. There was a simple caption - _Who is Jeff Winger's mystery companion?_

 _No - it can't be true_ , Annie thought as a feeling of sick despair came over her. But then she saw the name of the restaurant over the door and all her doubts vanished. _Of course you'd take her there. You know it's the one place I'd never go near._

"What do you want to do Annie?" Troy asked softly.

At the sight of the restaurant's name over the door Annie's feeling of despair had been replaced with a red mist of rage. "Get your toolkit Troy, we're going on a mission!" She ground out.

XXXXXX

"-And not only did he get all the charges dropped, but Jeff here-" Mark said, pointing at him "-managed to convince the judge that stripping was tax-deductable performance art and his client deserved a refund!" The entrees had been cleared away and Mark was regaling the new attorneys with anecdotes of the duo's more outrageous cases - most of which seemed to be Jeff's, for some reason.

Jeff grinned modestly as Chloe and Michaela laughed at Mark's anecdote. "Hey, fate had already dealt her one losing hand, being a stripper and all. There was no need to pile on the misery."

"Heart of gold, this guy." Mark mockingly saluted him with a wine glass.

"That's defamation of character, Petrocelli." Jeff grinned back, raising his Scotch glass.

"What's going on over there?" Mark had turned to face the door, where a scuffle seemed to have broken out. Jeff turned in time to see Annie slip past the maitre d', who was being blocked by Abed, and stampede over towards him.

"Annie, hi what are you-" was all Jeff managed to get out.

"What the hell is going on here?" Annie hissed. "You really think that if you brought your floozy here I wouldn't find out? You - you - pig!" She grabbed the Scotch out of Jeff's unresisting hand and tossed it in his face. "No wonder you wouldn't introduce me to anyone as your girlfriend, or take me to… meet… your…" Annie ground to a halt as she realised Jeff and Michaela weren't the only ones sitting at the table.

As Jeff dabbed at the Scotch dripping off his face with a napkin, he took one look at Annie whose expression was rapidly shifting from one of rage and pain to mortified embarrassment.

His own rapidly building rage died as he saw the expression on her face. _Oh boy, I've really messed this one up, haven't I?_ He thought as he remembered several conversations with Britta along the lines of how Annie wasn't a girl he could take half measures with, combined it with how… out of sorts she'd been since he'd seen her wedding album. Processing this, he took another look at her face and realising only one answer was possible, waved off the maitre d' who had managed to get past Abed and scurry over.

"Annie-" he pointed at the others. "This is Mark, Chloe and Michaela. We all work at the firm and we were celebrating Chloe and Michaela passing the bar exam." Looking somewhat bemused, the others waved.

"Guys," Jeff said, taking Annie's hand. "This is Annie, my girlfriend." Her expression shifted from mortification to surprise and finally happiness as a smile spread across it. "She's nuts of course, but I wouldn't have her any other way. Let's get you a chair and you can join us for dessert-" Jeff gestured to the somewhat disgruntled Maitre d'.

"Just a minute," Annie made a frantic thumbs up gesture to Abed, who was standing outside the window. Her friend's eyes went wide for a moment, then he disappeared in a dead sprint in the direction of Jeff's car.

XXXXXX

 _Now that MR WINGER has publicly committed himself to MISS EDISON is the path clear for them to live happily ever after, or are there yet obstacles unforeseen? Tune in next time on..._

(Author's note: my original plan for this storyline was for a series of self contained stories set in the same continuity but still readable as standalone ventures. Part 1 - J/A meet; Part 2 - they get into a relationship; Part 3 - ?. I do have some ideas for Part 3 but no overarching plot as yet, until one does emerge with evidence to the contrary (or not) please assume Happily Ever After:-))


End file.
